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Volumn 8, Issue 13, 2010, Pages 3015-3024

Brucine N-oxide-catalyzed Morita-Baylis-Hillman reaction of vinyl ketones: A mechanistic implication of dual catalyst system with proline

Author keywords

[No Author keywords available]

Indexed keywords

ARYL ALDEHYDES; CATALYST SYSTEM; COCATALYST; CONJUGATE ADDITION; ELECTRON-DEFICIENT; ENOLATES; HIGH ENANTIOSELECTIVITY; IMINIUM; MORITA-BAYLIS-HILLMAN REACTION; RATE DETERMINING STEP; REACTION CONVERSION; REACTION PARTNERS; SYNTHETIC UTILITY; TRANSITION STATE; VINYL KETONES;

EID: 77953799844     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c003667f     Document Type: Article
Times cited : (25)

References (43)
  • 26
    • 4744362831 scopus 로고
    • 1-Methylimidazole 3-N-oxide in MBH reaction, see:
    • S. E. Drewes G. H. P. Roos Tetrahedron 1988 44 4653 4670
    • (1988) Tetrahedron , vol.44 , pp. 4653-4670
    • Drewes, S.E.1    Roos, G.H.P.2
  • 28
    • 77953735076 scopus 로고    scopus 로고
    • Proline and brucine N-oxide are not particularly soluble in 1,4-dioxane, thus it is difficult to gauge the concentration of both catalysts In protic solvents, low enantioselectivity was observed (0-10% ee)
    • K. -S. Park J. Kim H. Choo Y. Chong Synlett 2007 395 398
    • (2007) Synlett , pp. 395-398
    • P, K.-S.1    Kim, J.2    Choo, H.3    Chong, Y.4
  • 31
    • 54749140370 scopus 로고    scopus 로고
    • We assigned stereoisomers of oxazolidinone based on the stability issue of oxazolidinones, see:
    • T. Mandal C. -G. Zhao Angew. Chem., Int. Ed. 2008 47 7714 7717
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 7714-7717
    • Mandal, T.1    Z, C.-G.2
  • 37
    • 33750508755 scopus 로고    scopus 로고
    • To increase the concentration of oxazolidinone 9, we examined 10 mol % of (S)-2-(5-tetrazolyl)pyrrolidine instead of (l)-proline, but the MBH product with low enantioselectivity was observed (17% ee) with a similar reactivity (10% conversion at 24 h at ambient temperature)
    • A. Aguirre-Valderrama J. A. Dobado J. Carbohydr. Chem. 2006 25 557 594
    • (2006) J. Carbohydr. Chem. , vol.25 , pp. 557-594
    • Aguirre-Valderrama, A.1    Dobado, J.A.2
  • 42
    • 37849014325 scopus 로고    scopus 로고
    • -1. For a comprehensive list of A-values, see: A more pronounced mis-matched case with (d)-proline and Miller's peptide catalyst has been evidenced, see: ref. 2g and 13 Addition of water is known to suppress the formation of oxazolidinone 9 in proline-catalyzed aldol reactions, see: ref. 18 The solubility of brucine N-oxide improved in the presence of methyl vinyl ketone and proline, see the Supporting Information Racemic MBH product, 8a, was obtained after 5 days in 10-20% yields due to the hydrolysis of imines to 2-nitrobenzaldehyde
    • R. Robiette V. K. Aggarwal J. N. Harvey J. Am. Chem. Soc. 2007 129 15513 15525
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 15513-15525
    • Robiette, R.1    Aggarwal, V.K.2    Harvey, J.N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.