메뉴 건너뛰기




Volumn 63, Issue 20, 1998, Pages 7078-7082

A superior, readily available enantiopure ligand for the catalytic enantioselective addition of diethylzinc to a-substituted aldehydes

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0000914701     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981336i     Document Type: Article
Times cited : (117)

References (39)
  • 5
    • 0002578608 scopus 로고
    • Ojima, I., Ed.; VCH Publishers: New York
    • Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp 159-202.
    • (1993) Catalytic Asymmetric Synthesis , pp. 159-202
    • Jacobsen, E.N.1
  • 9
    • 33646809211 scopus 로고    scopus 로고
    • (S)-Triphenylethylene oxide (3) is obtained in 94% ee following Jacobsen's epoxidation procedure and can be enantiomerically enriched by a single «crystallization from hexane up to >99.9% ee.
    • (S)-Triphenylethylene oxide (3) is obtained in 94% ee following Jacobsen's epoxidation procedure and can be enantiomerically enriched by a single «crystallization from hexane up to >99.9% ee.
  • 11
    • 33646789672 scopus 로고    scopus 로고
    • note
    • The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
  • 12
    • 33646815878 scopus 로고    scopus 로고
    • The ring-opening process was assumed to occur with complete stereospecifity in the other substrates.
    • The ring-opening process was assumed to occur with complete stereospecifity in the other substrates.
  • 13
    • 4244117250 scopus 로고
    • For reviews, see: (a) Soai, K. Chem. Rev. 1992, 92, 833-856.
    • (1992) Chem. Rev. , vol.92 , pp. 833-856
    • Soai, K.1
  • 15
    • 33646788633 scopus 로고    scopus 로고
    • A 2-3% increase in ee was observed with 4b-d under similar conditions.
    • A 2-3% increase in ee was observed with 4b-d under similar conditions.
  • 16
    • 33646792813 scopus 로고    scopus 로고
    • note
    • The S configuration was established by comparison of the optical rotation with published values and, for 6t, by comparison of retention times of the corresponding acetate derivative (GC, β-DEX column). For 6b, f, h, r the S configuration has been assumed.
  • 29
    • 0026650218 scopus 로고
    • For the use of bis-sulfonamidcs derived from enantiomerically pure trans1, 2-diaminocyclohexane as ligands for the highly efficient addition of diethylzinc to a limited set of aldehydes (four specimens), see: Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691-5700.
    • (1992) Tetrahedron , vol.48 , pp. 5691-5700
    • Takahashi, H.1    Kawakita, T.2    Ohno, M.3    Yoshioka, M.4    Kobayashi, S.5
  • 30
    • 33646808837 scopus 로고    scopus 로고
    • The configuration of the resulting alcohols is in agreement with Noyori's empirical rule. See ref lOb, pp 265-266.
    • The configuration of the resulting alcohols is in agreement with Noyori's empirical rule. See ref lOb, pp 265-266.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.