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Volumn 46, Issue 11, 2007, Pages 1878-1880

A way to highly enantiomerically enriched aza-Morita-Baylis-Hillman-type products

Author keywords

Aldehydes; Asymmetric synthesis; Enamines; Imines; Organocatalysis

Indexed keywords

ALDEHYDES; ESTERS; ISOMERIZATION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 34249712553     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603973     Document Type: Article
Times cited : (147)

References (31)
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    • Angew. Chem. Int. Ed. 2006, 45, 3689.
    • (2006) Chem. Int. Ed , vol.45 , pp. 3689
    • Angew1
  • 16
    • 0000804599 scopus 로고    scopus 로고
    • Routes other than aza-MBH reactions have been developed to access aza-MBH-type products with β-substituted α,β-unsaturated carbonyl moieties, but there has been no report of enantioselective versions of these reactions: a J. L. G. Ruano, I. Fernandez, M. P. Catalina, J. A. Hermoso, J. Sanz-Aparicio, M. Martinez-Ripoll, J. Org. Chem. 1998, 63, 7157;
    • Routes other than aza-MBH reactions have been developed to access aza-MBH-type products with β-substituted α,β-unsaturated carbonyl moieties, but there has been no report of enantioselective versions of these reactions: a) J. L. G. Ruano, I. Fernandez, M. P. Catalina, J. A. Hermoso, J. Sanz-Aparicio, M. Martinez-Ripoll, J. Org. Chem. 1998, 63, 7157;
  • 25
    • 33745711837 scopus 로고    scopus 로고
    • Whereas aza-MBH-type product 3 was generated by the formation of a C-C bond at the α-position of aldehyde 1, for the reaction between two molecules of 1 in the presence of proline, the γ-position of 1 reacted as a nucleophilic carbon atom and [3+3] adducts were formed. This observation supports the proposed formation of an enamine from 1 with proline: B.-C. Hong, M.-F. Wu, H.-C. Tseng, J.-H. Liao, Org. Lett. 2006, 8, 2217;
    • a) Whereas aza-MBH-type product 3 was generated by the formation of a C-C bond at the α-position of aldehyde 1, for the reaction between two molecules of 1 in the presence of proline, the γ-position of 1 reacted as a nucleophilic carbon atom and [3+3] adducts were formed. This observation supports the proposed formation of an enamine from 1 with proline: B.-C. Hong, M.-F. Wu, H.-C. Tseng, J.-H. Liao, Org. Lett. 2006, 8, 2217;
  • 26
    • 33749527371 scopus 로고    scopus 로고
    • formation of enamine intermediates of β-substituted α,β-unsaturated aldehydes with a pyrrolidine derivative was also suggested in a γ-amination reaction: S. Bertelsen, M. Marigo, S. Brandes, P. Diner, K. A. Jorgensen, J. Am. Chem. Soc. 2006, 128, 12 973.
    • b) formation of enamine intermediates of β-substituted α,β-unsaturated aldehydes with a pyrrolidine derivative was also suggested in a γ-amination reaction: S. Bertelsen, M. Marigo, S. Brandes, P. Diner, K. A. Jorgensen, J. Am. Chem. Soc. 2006, 128, 12 973.
  • 29
    • 34250808162 scopus 로고    scopus 로고
    • 1H NMR signals of 7 was observed with imidazole.
    • 1H NMR signals of 7 was observed with imidazole.
  • 30
    • 0036134467 scopus 로고    scopus 로고
    • Imidazole has been used or suggested as a nucleophile in MBH reactions in the presence of proline: a M. Shi, J.-K. Jiang, C.-Q. Li, Tetrahedron Lett. 2002, 43, 127;
    • Imidazole has been used or suggested as a nucleophile in MBH reactions in the presence of proline: a) M. Shi, J.-K. Jiang, C.-Q. Li, Tetrahedron Lett. 2002, 43, 127;


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.