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Volumn 2, Issue 24, 2000, Pages 3773-3776

Chiral Sulfonamide Induced Enantioselective Protonation of Samarium Enolate in the Reaction of α,β-Unsaturated Ester with Ketone

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EID: 0001538886     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006429c     Document Type: Article
Times cited : (41)

References (54)
  • 44
    • 85037519560 scopus 로고    scopus 로고
    • note
    • It has been reported that extremely high enantioselectivity (99%) was obtained in the enantioselective protonation of a lithium enolate of a thiol ester by using N-isopropylephedrine as a chiral proton source, see: refs 2t and 3h.
  • 46
    • 85037512601 scopus 로고    scopus 로고
    • note
    • The enantioselectivity was lowered when 4.0 equiv of HMPA was used in the reaction. For example, with this amount of HMPA as an additive, only 13% ee was obtained in the case of protonation using 8 as the chiral proton source.
  • 47
    • 85037492231 scopus 로고    scopus 로고
    • note
    • Due to the high oxophilicity and high coordination number of samarium, the chiral proton source, HMPA, and solvent THF are probably coordinated to the samarium ion in the transition state.
  • 48
    • 85037511771 scopus 로고    scopus 로고
    • note
    • 2: C 80.93, H 6.39. Found: C 80.73, H 6.50.
  • 49
    • 0000478917 scopus 로고
    • One important strategy for preparing α-substituted-γ-butyrolactone is stereoselective alkylation of lithium enolate of γ-butyrolactone, for examples, see: (a) Hanessian, S.; Murray, P. J. Org. Chem. 1987, 52, 1170-1172.
    • (1987) J. Org. Chem. , vol.52 , pp. 1170-1172
    • Hanessian, S.1    Murray, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.