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Volumn , Issue 19, 2005, Pages 3283-3286

A stereoselective oxy-Michael approach to THP*-protected β-hydroxy esters

Author keywords

hydroxy esters; Asymmetric synthesis; Oxy Michael additions; Protodesulfonylation; Samarium(II) iodide

Indexed keywords

ADDITION REACTIONS; CHROMATOGRAPHY; ISOMERS; REACTION KINETICS; SILICA GEL;

EID: 29044438003     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918484     Document Type: Article
Times cited : (7)

References (30)
  • 14
    • 0000376088 scopus 로고
    • For a leading example of catalytic asymmetric aldol approaches to β-hydroxy esters, see: (a) Carreira, E. M.; Singer, R. A.; Lee, W. S. J. Am. Chem. Soc. 1994, 116, 8837.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 8837
    • Carreira, E.M.1    Singer, R.A.2    Lee, W.S.3
  • 15
    • 47749122232 scopus 로고    scopus 로고
    • VCH-Wiley: Weinheim, Chap. 6
    • For references of organocatalytic asymmetric aldol approaches to β-hydroxy esters, see: (b) Berkessel, A.; Gröger, H. Asymmetric Organocatalysis; VCH-Wiley: Weinheim, 2005, Chap. 6, 140-166.
    • (2005) Asymmetric Organocatalysis , pp. 140-166
    • Berkessel, A.1    Gröger, H.2
  • 26
    • 29044442535 scopus 로고    scopus 로고
    • note
    • Studies by us have indicated that the direct stereoselective oxy-Michael addition to αβ-unsaturated esters (such as tertbutyl crotonate) was not a viable way to synthesise protected aldol products owing to the low natural reactivity of the two components.
  • 27
    • 29044434331 scopus 로고    scopus 로고
    • note
    • All the sulfone-derived Michael acceptors 2 and 5 were obtained as a mixture Z/E isomers with the predominant E configuration assigned by NOE.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.