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Volumn 48, Issue 45, 2009, Pages 8572-8574

Brønsted acid catalyzed enantioselective semipinacol rearrangement for the synthesis of chiral spiroethers

Author keywords

Asymmetric catalysis; Br nsted acids; Rearrangements; Semipinacols; Spirocompounds

Indexed keywords

ALLYLIC ALCOHOL; ASYMMETRIC CATALYSIS; CATALYTIC AMOUNTS; ENANTIOSELECTIVE; REARRANGEMENT REACTIONS; REARRANGEMENTS; SEMIPINACOLS; SILVER SALTS; SPIROCOMPOUNDS;

EID: 70350346454     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200904565     Document Type: Article
Times cited : (170)

References (65)
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    • For reviews on the semipinacol rearrangement, see : a) B. Rickborn, in Comprehensive Organic Synthesis, Vol.3 (Ed. : B. M. Trost), Pergamon, Oxford, 1991, p. 733;
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 733
    • Rickborn, B.1
  • 27
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    • For the related palladium- and gold-catalyzed asymmetric Wagner-Meerwein rearrangements, see : a) B. M. Trost, T. Yasukata, J. Am. Chem Soc. 2001, 123, 7162;
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  • 36
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    • For the asymmetric synthesis of spiroethers, see Refs [3] and [4]
    • For the asymmetric synthesis of spiroethers, see Refs [3] and [4].
  • 37
    • 0346865819 scopus 로고    scopus 로고
    • For reviews on chiral Brønsted acid catalysis, see: a) P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289;
    • (2003) Chem. Soc. Rev. , vol.32 , pp. 289
    • Schreiner, P.R.1
  • 42
    • 33845477631 scopus 로고    scopus 로고
    • For reviews on chiral phosphoric acids, see: a) S. J. Connon, Angew. Chem 2006, 118, 4013;
    • (2006) Angew. Chem , vol.118 , pp. 4013
    • Connon, S.J.1
  • 43
  • 47
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    • For selected examples of phosphoric acid catalyzed reactions, see: a) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356;
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 5356
    • Uraguchi, D.1    Terada, M.2
  • 62
    • 67749118135 scopus 로고    scopus 로고
    • For a recent example of a chiral Brønsted acid catalyzed intermolecular addition of an enol ether via oxocarbonium ion, see: M. Terada, H. Tanaka, K. Sorimachi, J. Am. Chem. Soc. 2009, 131, 3430.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 3430
    • Terada, M.1    Tanaka, H.2    Sorimachi, K.3
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    • note
    • The proposed pathway on the semipinacol rearrangement of 2oxo allylic alcohol 1 a under the catalysis of silver phosphate (R)2f was depicted as follows, in which, the in situ generation of (R)2e was performed by silver-proton exchange between the alcohol and silver phosphate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.