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Volumn , Issue 17, 1999, Pages 2525-2535

The generation of difluoroenolates from trifluoroethanol and reproducible syntheses of α,α-difluoro-β-hydroxy ketones

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EID: 0002138648     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a902966d     Document Type: Article
Times cited : (27)

References (33)
  • 26
    • 33746403117 scopus 로고    scopus 로고
    • 1990, 704. For a similar application see £.'T. Patel, J. M. Percy and R. D. Wilkes, Tetrahedron, 1995,51, 9201.
    • M. Schlosser, T. Jenny and Y. Guggisberg, Synlelt, 1990, 704. For a similar application see £.'T. Patel, J. M. Percy and R. D. Wilkes, Tetrahedron, 1995,51, 9201.
    • T. Jenny and Y. Guggisberg, Synlelt
    • Schlosser, M.1
  • 27
    • 33746399186 scopus 로고    scopus 로고
    • 1921, 119, 305
    • Described originally by Ingold (C. K. Ingold, J. Client. Soc., 1921, 119, 305), the effect is discussed more widely in the context of intramolecular reactions by Kirby (
    • J. Client. Soc.
    • Ingold, C.K.1
  • 28
    • 77956770660 scopus 로고    scopus 로고
    • 1980, 17, 183
    • A. J. Kirby, Adv. Phys. Org. Chem., 1980, 17, 183). A number of examples exist in which the addition of a second alkyl group (creating a gem-pah) results in cyclisation rate increases of 102.
    • Adv. Phys. Org. Chem.
    • Kirby, A.J.1
  • 30
    • 0000832426 scopus 로고    scopus 로고
    • 1990, 55, 5680.
    • S. Sengupta and V. Snieckus, J. Org. Chem., 1990, 55, 5680. Transacylation could not be stopped in the desfluorosystem. Rapid (<5 s after the addition of carbonyl electrophile) quenching allowed methyl ketones to be isolated; more protracted reactions yielded aldol products. For a review of a-heteroatom substituted alk-Ienyllithium reagents,
    • J. Org. Chem.
    • Sengupta, S.1    Snieckus, V.2
  • 32
    • 33746469774 scopus 로고    scopus 로고
    • note
    • -1, 24046 reflections measured, 3911 unique (A(int) = 0.0556) which were used in all calculations. The final wR(F2) was 0.1512 (all data). CCDC reference number 207/350. See http://www.rsc.org/ suppdata/pl/1999/2525 for crystallographic files in .cif format.
  • 33
    • 0000444632 scopus 로고    scopus 로고
    • 1990, 55, 3982
    • There are few examples of 1,4-asymmetric induction in reactions of this type. Sengupta and Snieckus (réf. 29) reported a 4:1 excess of one diastereoisomeric series, though the 1,4-reIationship (syn or anti) was not known. See also B. M. Trost and H. Urabe, J. Org. Client., 1990, 55, 3982 for an example of 1,4-asymmetric induction in a Mukaiyama aldol reaction.
    • J. Org. Client.
    • Trost, B.M.1    Urabe, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.