UBFQQO

Organic Chemistry Section

Department of Inorganic and Organic Chemistry

Chapters of Books


Basic research Modern Methods in Stereoselective Aldol Reactions
by Rainer Mahrwald Editor
Chapter 1. Stereoselective Acetate Aldol Reactions
Pedro Romea and Fèlix Urpí.
Pages 1-81
Wiley, 2013


Organic Syntheses
Stereoselective Synthesis of anti α-Methyl-β-Methoxy Carboxylic Compounds
Pedro Romea and Fèlix Urpí.
Volume 90
Pages 182-189
Organic Syntheses, 2013

e-EROS Encyclopedia of Reagents for Organic Synthesis
Trichlorotitanium isopropoxide
Pedro Romea and Fèlix Urpí.
e-EROS, 2008


Articles


84. Direct and Asymmetric Aldol Reactions of N-Azidoacetyl-1,3-thiazolidine-2-thione Catalyzed by Chiral Nickel(II) Complexes. A New Approach to the Synthesis of β-Hydroxy-α-Amino Acids
Teloxa, S. F.; Mellado-Hidalgo, M.; Kennington, S. C. D.; Romea, P.; Urpí, F.; Aullón, G.; Font-Bardia, M.
Chem. Eur. J. 2022, 28, in press.
83. Synthesis of [(R)-DTBM-SEGPHOS]NiCl2 for the Enantioselective Acetal Formation from N-Propanoyl-1,3-Thiazinane-2-thione and Trimethyl Orthoformate
Kennington, S. C. D.; Romea, P.; Urpí, F.
Org. Synth. 2022, 99, 1-14.
82. Stereoselective Alkylation of Chiral Titanium(IV) Enolates with tert-Butyl Peresters
Pérez-Palau, M.; Sanosa, N.; Romea, P.; Urpí, F.; López, R.; Gómez-Bengoa, E.; Font-Bardia, M.
Org. Lett. 2021, 23, 8852-8856.
81. Synthesis and Acylation of 1,3-Thiazinane-2-thione
Kennington, S. C. D.; Galeote, O.; Mellado-Hidalgo, M.; Romea, P.; Urpí, F.
Org. Synth. 2021, 98, 374-390.
80. Direct, Enantioselective, and Nickel(II) Catalyzed Reactions of Direct and Enantioselective Aldol Reactions Catalyzed by Chiral Nickel(II) Complexes
Kennington, S. C. D.; Teloxa, S. F.; Mellado-Hidalgo, M.; Galeote, O.; Puddu, S.; Bellido, M.; Romea, P.; Urpí, F.; Aullón, G.; Font-Bardia, M.
Angew. Chem. Int. Ed. 2021, 60, 15307-15312.
79. Direct, Enantioselective, and Nickel(II) Catalyzed Reactions of N-Azidoacetyl Thioimides with Trimethyl Orthoformate. A New Combined Methodology for the Rapid Synthesis of Lacosamide and Derivatives
Teloxa, S. F.; Kennington, S. C. D.; Camats, M.; Romea, P.; Urpí, F.; Aullón, G.; Font-Bardia, M.
Chem. Eur. J. 2020, 26, 11540-11548.
78. Stereoselective Decarboxylative Alkylation of Titanium(IV) Enolates with Diacyl Peroxides
Gómez-Palomino, A.; Pérez-Palau, M.; Romea, P.; Urpí, F.; Del Olmo, M.; Hesse, T.; Fleckenstein, S.; Gómez-Benoga, E.; Sotorríos, L.; Font-Bardia, M.
Org. Lett. 2020, 22, 199-203.
77. Direct anti Glycolate Aldol Reaction of Protected Chiral N‐Hydroxyacetyl Thiazolidinethiones with Acetals Catalyzed by a Nickel(II) Complex
Romo, J. M.; Romea, P.; Urpí, F.
Eur. J. Org. Chem. 2019, 6296-6305.
76. Stereoselective Synthesis of Protected Peptides Containing an anti β-Hydroxy Tyrosine
Fernández-Valparis, J.; Romea, P.; Urpí, F.
Eur. J. Org. Chem. 2019, 2745-2752.
75. Direct and Asymmetric Nickel(II)-Catalyzed Construction of Carbon−Carbon Bonds from N‐Acyl Thiazinanethiones
Kennington, S. C. D.; Taylor, A. J.; Romea, P.; Urpí, F.; Aullón, G.; Font-Bardia, M.; Ferré, L.; Rodrigalvarez, J.
Org. Lett. 2019, 21, 305-309.
74. General and Stereoselective Aminoxylation of Biradical Titanium(IV) Enolates with TEMPO: a Detailed Study on the Effect of the Chiral Auxiliary
Kennington, S. C. D.; Gómez-Palomino, A.; Salomó, E.; Romea, P.; Urpí, F.; Font-Bardia, M.
Org. Biomol. Chem. 2018, 16, 4807-4815.
73. Stereoselective Oxidation of Titanium(IV) Enolates with Oxygen
Gómez-Palomino, A.; Romea, P.; Urpí, F.; Font-Bardia, M.
Synthesis 2018, 50, 2721-2726.
72. Stereoselective and Catalytic Synthesis of anti β-Alkoxy-α-Azido Carboxylic Derivatives
Fernández-Valparís,J.; Romea, P.; Urpí, F.; Font-Bardia, M.
Org. Lett. 2017, 19, 6400-6403.
71. Substrate–Controlled Michael Additions of Titanium Enolates from Chiral α-Benzyloxy Ketones to Conjugated Nitroalkenes
Gómez-Palomino, A.; Barrio, A.; García-Lorente, P.; Romea, P.; Urpí, F.; Font-Bardia, M.
Eur. J. Org. Chem. 2017, 5776-5784.
70. Experimental and Computational Evidence of the Biradical Structure and Reactivity of Titanium(IV) Enolates
Heras, C.; Gómez-Palomino, A.; Romea, P.; Urpí, F.; Bofill, J. M.; Moreira, I. de P. R.
J. Org. Chem. 2017, 82, 8909-8916.
69. Diastereoselective and Catalytic α-Alkylation of Chiral N-Acyl Thiazolidinethiones with Stable Carbocationic Salts
Kennington, S. C. D.; Ferrè, M.; Romo, J. M.; Romea, P.; Urpí, F.; Font-Bardia, M.
J. Org. Chem. 2017, 82, 6426-6433.
68. Total Synthesis of (+)-Herboxidiene/GEX 1A
Gómez-Palomino, A.; Pellicena, M.; Krämer, K.; Romea, P.; Urpí, F.; Aullón, G.; Padrón, J. M.
Org. Biomol. Chem. 2017, 15, 1842-1862.
67. Substrate-controlled Aldol Reactions from Chiral α-Hydroxy Ketones
Aullón, G.; Romea, P.; Urpí, F.
Synthesis 2017, 49, 474-503.
66. Stereoselective Synthesis of the C9–C19 Fragment of Peloruside A
Kennington, S.C.D.; Romo, J.M.; Romea, P.; Urpí, F.
Org. Lett. 2016, 18, 3018-3021.
65. Studies towards the synthesis of tedanolide C. Construction of the C13-epi C1–C15 fragment
Zambrana, J.; Romea, P.; Urpí, F.
Org. Biomol. Chem. 2016, 14, 5219-5223.
64. Stereoselective Alkylation of (S)-N-Acyl-4-isopropyl-1,3-thiazolidine-2-thiones Catalyzed by (Me3P)2NiCl2
Fernández-Valparís, J.; Romo, J. M.; Romea, P.; Urpí, F.; Kowalski, H.; Font-Bardia, M.
Org. Lett. 2015, 17, 3540-3543.
63. Kinetic resolution of esters from secondary and tertiary benzylic propargylic alcohols by an improved esterase-variant from Bacillus sp. BP-7
Fillat, A.; Romea, P.; Pastor, F. I. J.; Urpí, F.; Díaz, P.
Catalysis Today 2015, 255, 16-20.
62. Stereoselective Acetate Aldol Reactions of α-Silyloxy Ketones
Lorente, A.; Pellicena, M.; Romea, P.; Urpí, F.
Tetrahedron 2015, 71, 1023-1035.
61. Substrate-Controlled Michael Additions of Chiral Ketones to Enones
Fàbregas, M.; Gómez-Palomino, A.; Pellicena, M.; Reina, D. F.; Romea, P.; Urpí, F.; Font-Bardia, M.
Org. Lett. 2014, 16, 6220-6223.
60. Stereoselective Aminoxylation of Biradical Titanium Enolates with TEMPO
Gómez-Palomino, A.; Pellicena, M.; Romo, J. M.; Solà, R.; Romea, P.; Urpí, F.; Font-Bardia, M.
Chem. Eur. J. 2014, 20, 10153-10159.
59. Stereoselective Titanium-Mediated Aldol Reactions of a Chiral Lactate-Derived Ethyl Ketone with Ketones
Alcoberro, S.; Gómez-Palomino, A.; Solà, R.; Romea, P.; Urpí, F.; Font-Bardia, M.
Org. Lett. 2014, 16, 584-587.
58. Improving enantioselectivity towards tertiary alcohols using mutants of Bacillus sp. BP-7 esterase EstBP7 holding a rare GGG(X)-oxyanion hole
Fillat, A.; Romea, P.; Urpí, F.; Pastor, F. I. J.; Diaz, P.
Appl. Microbiol. Biotechnol. 2014, 98, 4479-4490.
57. Diastereoselective Methyl Orthoformate Alkylations of Chiral N-Acyl Thiazolidinethiones Catalyzed by Nickel(II) Complexes
Gálvez, E.; Romo, J. M.; Nubiola, I.; Romea, P.; Urpí, F.; Kindred, M.
Adv. Synth. Catal. 2013, 355, 2781-2786.
56. Stereoselective titanium-mediated aldol reactions from a chiral isopropyl ketone
Zambrana, J.; Romea, P.; Urpí, F.
Chem. Commun. 2013, 49, 4507-4509.
55. Stereoselective synthesis of C-glycosides by addition of titanium enolates from a chiral N-glycolyl thiazolidinethione to glycals
Gálvez, E.; Sau, M.; Romea, P.; Urpí, F.; Font-Bardia, M.
Tetrahedron Lett. 2013, 54, 1467-1470.
54. Stereoselective titanium-mediated aldol reactions of α-benzyloxy methyl ketones
Pellicena, M.; Solsona, J. G.; Romea, P.; Urpí, F.
Tetrahedron 2012, 68, 10338-10350.
53. Diastereoselective Additions of Titanium Enolates from N-Glycolyl Thiazolidinethiones to Acetals
Baiget, J.; Caba, M.; Gálvez, E.; Romea, P.; Urpí, F.; Font-Bardia, M.
J. Org. Chem. 2012, 77, 8809-8814.
52. Stereoselective Synthesis of protected 3-amino-3,6-dideoxyaminosugars
Nebot, J.; Romea, P.; Urpí, F.
Org. Biomol. Chem. 2012, 10, 6395-6403.
51. Total Synthesis of (+)-Herboxidiene from Two Chiral Lactate-derived Ketones
Pellicena, M.; Krämer, K.; Romea, P.; Urpí, F.
Org. Lett. 2011, 13, 5350-5353.
50. Highly Stereoselective Titanium-mediated Aldol Reaction from (S) 4-Benzyloxy-3-methyl-2-butanone
Zambrana, J.; Romea, P.; Urpí, F.; Luján, C.
J. Org. Chem. 2011, 76, 8575-8587.
49. Highly stereoselective titanium-mediated aldol reactions from chiral α-silyloxy ketones. A reliable tool for the synthesis of natural products
Esteve, J.; Jiménez, C.; Nebot, J.; Velasco, J.; Romea, P.; Urpí, F.
Tetrahedron 2011, 67, 6045-6056.
48. Stereoselective Acetate Aldol Reactions from Metal Enolates
Ariza, X.; Garcia, J.; Romea, P.; Urpí, F.
Synthesis 2011, 2175-2191.
47. Synthesis and Biological Evaluation of 1-Deoxy-5-hydroxysphingosine Derivatives
Esteve, J.; Lorente, A.; Romea, P.; Urpí, F.; Ríos-Luci,C.; Padrón, J. M.
Eur. J. Org. Chem. 2011, 960-967.
46. Highly Stereoselective Synthesis of syn-1,3-Diols through a Sequential Titanium-Mediated Aldol Reaction and LiBH4 Reduction
Esteve, J.; Matas, S.; Pellicena, M.; Velasco, J.; Romea, P.; Urpí, F.; Font-Bardia, M.
Eur. J. Org. Chem. 2010, 3146-3151.
45. 1,4-syn-Asymmetric induction in the titanium-mediated aldol reactions of chiral methyl α-silyloxy ketones
Lorente, A.; Pellicena, M.; Romea, P.; Urpí, F.
Tetrahedron Lett. 2010, 51, 942-945.
44. Stereoselective Synthesis of α- and β-C-Glycosides by Addition of Titanium Enolates to Glycals
Gálvez, E.; Larrosa, I.; Romea, P.; Urpí, F.
Synlett 2009, 2982-2986.
43. Stereoselective Synthesis of Highly Functionalized Structures from Lactate-Derived Halo Ketones
Nebot, J.; Romea, P.; Urpí, F.
J. Org. Chem. 2009, 74, 7518-7521.
42. New Approach to the Stereoselective Synthesis of Tertiary Methyl Ethers
Checa, B.; Gálvez, E.; Parelló, R.; Sau, M.; Romea, P.; Urpí, F.; Font-Bardia, M.; Solans, X.
Org. Lett. 2009, 11, 2193-2196.
41. Stereoselective Synthesis of anti α-Methyl-β-methoxy Carboxylic Compounds
Gálvez, E.; Romea, P.; Urpí, F.
Org. Synth. 2009, 86, 81-91.
40. Preparation of (S)-4-Isopropyl-N-propanoyl-1,3-thiazolidine-2-thione
Gálvez, E.; Romea, P.; Urpí, F.
Org. Synth. 2009, 86, 70-80.
39. Stereoselective addition of titanium enolates to functionalized acetals. A novel approach to the γ-amino acids of bistramides and FR252921
Gálvez, E.; Parelló, R.; Romea, P.; Urpí, F.
Synlett 2008, 2951-2954.
38. 1,4-Asymmetric induction in the titanium-mediated aldol reactions of α-benzyloxy methyl ketones
Pellicena, M.; Solsona, J. G.; Romea, P.; Urpí, F.
Tetrahedron Lett. 2008, 49, 5265-5267.
37. On the influence of chiral auxiliaries in the stereoselective cross-coupling reactions of titanium enolates and acetals
Baiget, J.; Cosp, A.; Gálvez, E.; Gómez-Pinal, L ; Romea, P.; Urpí, F.
Tetrahedron 2008, 64, 5637-5644.
36. Unconventional Biradical Character of Titanium Enolates
Moreira, I. de P. R.; Bofill, J. M.; Anglada, J. M.; Solsona, J. G.; Nebot, J.; Romea, P.; Urpí, F.
J. Am. Chem. Soc. 2008, 130, 3242-3243.
35. Synthesis of six-membered oxygenated heterocycles through carbon-oxygen bond-forming reactions
Larrosa, I.; Romea, P.; Urpí, F.
Tetrahedron 2008, 64, 2683-2723.
34. Highly Stereoselective TiCl4-Mediated Aldol Reactions from (S)-2-Benzyloxy-3-pentanone
Rodríguez-Cisterna, V.; Villar, C.; Romea, P.; Urpí, F.
J. Org. Chem. 2007, 72, 6631-6633.
33. Stereoselective titanium-mediated aldol reaction of (S)-2-tert-butyldimethylsilyloxy-3-pentanone
Nebot, J.; Figueras, S.; Romea, P.; Urpí, F.; Ji, Y.
Tetrahedron 2006, 62, 11090-11099.
32. Synthesis of the C9-C21 fragment of debromaplysiatoxin and oscillatoxins A and D
Cosp, A.; Llàcer, E.; Romea, P.; Urpí, F.
Tetrahedron. Lett. 2006, 47, 5819-5823.
31. Studies on the hydrogenolysis of benzyl ethers
Llàcer, E.; Romea, P.; Urpí, F.
Tetrahedron. Lett. 2006, 47, 5815-5818.
30. Stereoselective Synthesis of the Western Hemisphere of Salinomycin
Larrosa, I.; Romea, P.; Urpí, F.
Org. Lett. 2006, 8, 527-530.
29. Highly stereoselective aldol reaction based on titanium enolates from (S)-1-benzyloxy-2-methyl-3-pentanone
Solsona, J. G.; Nebot, J.; Romea, P.; Urpí, F.
J. Org. Chem. 2005, 70, 6533-6536.
28. A stereoselective aldol-reduction approach to polyoxygenated natural products. Synthesis of C1-C6 fragment of erythronolides
Galobardes, M.; Gascón, M.; Romea, P.; Urpí, F.
Lett. Org. Chem. 2005, 2, 312-315.
27. Double Stereodifferentiating Aldol Reactions Based on Chiral Ketones Derived from Lactic Acid: Synthesis of C1-C6 Fragment of Erythronolides
Solsona, J. G.; Nebot, J.; Romea, P.; Urpí, F.
Synlett 2004, 2127-2130.
26. Stereoselective titanium-mediated syn-aldol reaction from a lactate-derived chiral ethyl ketone
Solsona, J. G.; Romea, P.; Urpí, F.
Tetrahedron Lett. 2004, 45, 5379-5382.
25. Studies Directed toward the Construction of Polypropionate Fragment of Superstolide A
Solsona, J. G.; Romea, P.; Urpí, F.
Org. Lett. 2003, 5, 4681-4684.
24. Studies on the Intramolecular CH···X (X= O, S) Interactions in (S)-N-Acyl-4-isopropyl-1,3-thiazolidine-2-thiones and Related 1,3-Oxazolidin-2-ones
Cosp, A.; Larrosa, I.; Anglada, J. M.; Bofill, J. M.; Romea, P.; Urpí, F.
Org. Lett. 2003, 5, 2809-2812.
23. Synthesis of O-Benzyl Protected anti Aldols through the Cross-Coupling Reaction of Dibenzyl Acetal with a Chiral Titanium Enolate
Cosp, A.; Larrosa, I.; Vilasís, I.; Romea, P.; Urpí, F.; Vilarrasa, J.
Synlett 2003, 1109-1112.
22. Highly Stereoselective Aldol Reaction of Titanium Enolates from Lactate-Derived Chiral Ketones
Solsona, J. G.; Romea, P.; Urpí, F.; Vilarrasa, J.
Org. Lett. 2003, 5, 519-522.
21. Unprecedented Highly Stereoselective α- and β-C-Glycosidation with Chiral Titanium Enolates
Larrosa, I.; Romea, P.; Urpí, F.; Balsells, D.; Vilarrasa, J.; Font-Bardia, M.; Solans, X.
Org. Lett. 2002, 4, 4651-4654.
20. Stereoselective synthesis of syn,syn-2-methyl-1,3-diols through one pot aldol-reduction sequence
Galobardes, M.; Mena, M.; Romea, P.; Urpí, F.; Vilarrasa, J.
Tetrahedron Lett. 2002, 43, 6145-6148.
19. β3-Amino acids by nucleophilic ring-opening of N-nosyl aziridines
Farràs, J.; Ginesta, X.; Sutton, P.; Taltavull, J.; Egeler, F.; Romea, P.; Urpí, F.; Vilarrasa, J.
Tetrahedron 2001, 57, 7665-7674.
18. Enantiopure β-methoxy carboxyl derivatives from a chiral titanium enolate and dimethyl acetals
Cosp, A.; Romea, P.; Urpí, F.; Vilarrasa, J.
Tetrahedron Lett. 2001, 42, 4629-4631.
17. Enantioselective Addition of a Chiral Thiazolidinethione-Derived Titanium Enolate to Acetals
Cosp, A.; Romea, P.; Talavera, P.; Urpí, F.; Vilarrasa, J.; Font-Bardia, M.; Solans, X.
Org. Lett. 2001, 3, 615-617.
16. Simple and Efficient Preparation of Enantiopure Alkyl α-Hydroxyalkyl Ketones
Ferreró, M.; Galobardes, M.; Martín, R.; Montes, T.; Romea, P.; Rovira, R.; Urpí, F.; Vilarrasa, J.
Synthesis 2000, 1608-1614.
15. Pseudoaxially Disubstituted Cyclo-β3-tetrapeptide Scaffolds
Sutton, P. W.; Bradley, A.; Farràs, J.; Romea, P.; Urpí, F.; Vilarrasa, J.
Tetrahedron 2000, 56, 7947-7958.
14. Enolization of Chiral α-Silyloxy Ketones with Dicyclohexylchloroborane. Application to Stereoselective Aldol Reactions
Galobardes, M.; Gascón, M.; Mena, M.; Romea, P.; Urpí, F.; Vilarrasa, J.
Org. Lett. 2000, 2, 2599-2602.
13. Reaction of Chiral Titanium Z-Enolates with Chiral α-Silyloxy Aldehydes. Syntheses of NFX-2 and Antimycinone
Esteve, C.; Ferreró, M.; Romea, P.; Urpí, F.; Vilarrasa, J.
Tetrahedron Lett. 1999, 40, 5083-5086.
12. Reaction of Achiral Titanium Z-Enolates with Chiral α-Silyloxy Aldehydes
Esteve, C.; Ferreró, M.; Romea, P.; Urpí, F.; Vilarrasa, J.
Tetrahedron Lett. 1999, 40, 5079-5082.
11. Design and synthesis of a novel cyclo-β-tetrapeptide
Sutton, P. W.; Bradley, A.; Elsegood, M. R. J.; Farràs, J.; Jackson, R. F. W.; Romea, P.; Urpí, F.; Vilarrasa, J.
Tetrahedron Lett. 1999, 40, 2629-2632.
10. Syntheses of the C-1 alkyl side chains of Zaragozic acids A and C
Bach, J.; Galobardes, M.; García, J.; Romea, P.; Tey, C.; Urpí, F.; Vilarrasa, J.
Tetrahedron Lett. 1998, 39, 6765-6768.
9. Simple and Efficient Preparation of Ketones from Morpholine Amides
Martín, R.; Romea, P.; Tey, C.; Urpí, F.; Vilarrasa, J.
Synlett 1997, 1414-1416.
8. Highly Stereoselective Aldol Reactions of Titanium Enolates from Ethyl α-Silyloxyalkyl Ketones
Figueras, S.; Martín, R.; Romea, P.; Urpí, F.; Vilarrasa, J.
Tetrahedron Lett. 1997, 38, 1637-1640.
7. A Simple Procedure for the Preparation of Enantiopure Ethyl α-Hydroxyalkyl Ketones
Martín, R.; Pascual, O.; Romea, P.; Rovira, R.; Urpí, F.; Vilarrasa, J.
Tetrahedron Lett. 1997, 38, 1633-1636.
6. Studies in Macrolide Synthesis: A Stereocontrolled Synthesis of Oleandolide Employing Reagent- and Substrate-Controlled Aldol Reactions of (S)-1-(Benzyloxy)-2-methylpentan-3-one
Paterson, I.; Norcross, R. D.; Ward, R. A.; Romea, P.; Lister, M. A.
J. Am. Chem. Soc. 1994, 116, 11287-11314.
5. Substrate-Controlled Aldol Reactions of Chiral Ethyl Ketones; Application to the Total Synthesis of Oleandomycin
Paterson, I.; Ward, R. A.; Romea, P.; Norcross, R. D.
J. Am. Chem. Soc. 1994, 116, 3623-3624.
4. Alternative Procedures for the Macrolactamisation of ω-Azido Acids
Bosch, I.; Romea, P.; Urpí, F.; Vilarrasa, J.
Tetrahedron Lett. 1993, 34, 4671-4674.
3. Improved Methods for the N-Nitration of Amides
Romea, P.; Aragonès, M.; García, J.; Vilarrasa, J.
J. Org. Chem. 1991, 56, 7038-7042.
2. A Fast Procedure for the Reduction of Azides and Nitro Compounds Based on the Reducing Ability of Sn(SR)3- Species
Bartra, M.; Romea, P.; Urpí, F.; Vilarrasa, J.
Tetrahedron 1990, 46, 587-594.
1. Nitrosation of Hindered Amides
Romea, P.; Urpí, F.; Vilarrasa, J.
J. Org. Chem. 1989, 54, 3209-3211.

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