Direct organocatalytic asymmetric Mannich-type reactions in aqueous media: One-pot Mannich-allylation reactions

Tetrahedron Letters

Volumn 44, Issue 9, 2003, Pages 1923-1926

  Córdova, Armando ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDIUM; PROLINE;

ALLYLATION; ARTICLE; CATALYST; COLUMN CHROMATOGRAPHY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MANNICH REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037463462     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00019-4     Document Type: Article

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29. For other Lewis acid-catalyzed asymmetric reactions in aqueous media, see: Diels-Alder: (b) Otto, S.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1999, 121, 6798; Aldol: (c) Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 11531; (d) Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165; Allylation: (e) Loh, T. P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261; Alkynation: (f) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638.
30. For other Lewis acid-catalyzed asymmetric reactions in aqueous media, see: Diels-Alder: (b) Otto, S.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1999, 121, 6798; Aldol: (c) Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 11531; (d) Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165; Allylation: (e) Loh, T. P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261; Alkynation: (f) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638.
31. For other Lewis acid-catalyzed asymmetric reactions in aqueous media, see: Diels-Alder: (b) Otto, S.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1999, 121, 6798; Aldol: (c) Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 11531; (d) Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165; Allylation: (e) Loh, T. P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261; Alkynation: (f) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638.
32. For other Lewis acid-catalyzed asymmetric reactions in aqueous media, see: Diels-Alder: (b) Otto, S.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1999, 121, 6798; Aldol: (c) Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 11531; (d) Kobayashi, S.; Hamada, T.; Nagayama, S.; Manabe, K. Org. Lett. 2001, 3, 165; Allylation: (e) Loh, T. P.; Zhou, J.-R. Tetrahedron Lett. 2000, 41, 5261; Alkynation: (f) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638.
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43. For organocatalytic Diels-Alder reactions in water, see: (a) Northrup, A. D.; Macmillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2460; (b) Thayumanavan, R.; Dhevalapally, B.; Sakthivel, K.; Tanaka, F.; Barbas, III, C. F. Tetrahedron Lett. 2002, 43, 3817 and Ref. 7. For organocatalytic aldol reactions in water, see: (c) Córdova, A.; Notz, W.; Barbas, III, C. F. Chem. Commun. 2002, 3024.
44. For organocatalytic Diels-Alder reactions in water, see: (a) Northrup, A. D.; Macmillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2460; (b) Thayumanavan, R.; Dhevalapally, B.; Sakthivel, K.; Tanaka, F.; Barbas, III, C. F. Tetrahedron Lett. 2002, 43, 3817 and Ref. 7. For organocatalytic aldol reactions in water, see: (c) Córdova, A.; Notz, W.; Barbas, III, C. F. Chem. Commun. 2002, 3024.
45. 4), filtered, concentrated and the residue purified by column chromatography (silica, hexanes/ethyl acetate mixtures) to afford the corresponding Mannich addition product. The ee's of all products were determined by chiral HPLC analysis.
46. β-Formyl functionalized amino acids can epimerize upon column chromatography, decreasing the dr. However, the crude products are stable upon storage at 0°C in EtOAc for months.
47. NMR, optical rotation and chiral-phase HPLC analysis of Mannich products 1-4, 7 and 8 were identical to those reported in Ref. 4f.
48. 3 (M+): 289.1673; found: 289.1675.
49. This procedure afforded 9 with a dr of 1:1 and 93% ee.