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Volumn 73, Issue 24, 2008, Pages 9727-9731

Nucleophilic carbene catalyzed synthesis of 1,2 amino alcohols via azidation of epoxy aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ACYL AZIDES; AMINO ALCOHOLS; ASYMMETRIC INDUCTIONS; AZIDATION; CARBAMOYL AZIDES; CARBENE; CATALYZED SYNTHESES; CHEMICAL EQUATIONS; COMPLEMENTARY SEQUENCES; CURTIUS REARRANGEMENTS; EPOXY ALDEHYDES; GOOD YIELDS; HYDROXY GROUPS; OXAZOLIDINONES; TRIAZOLIUM;

EID: 58049219098     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8020055     Document Type: Article
Times cited : (39)

References (61)
  • 6
    • 0002531006 scopus 로고
    • The Benzoin and Related Acyl Anion Equivalent Reactions
    • Trost, B. M, Fleming, I, Eds, Pergamon Press: Oxford
    • (b) Hassner, A. The Benzoin and Related Acyl Anion Equivalent Reactions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol, 1, p 541.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 541
    • Hassner, A.1
  • 7
    • 0000011522 scopus 로고    scopus 로고
    • Addition of acyl carbanion equivalents to carbonyl groups and enones
    • Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer-Verlag: Berlin, Germany
    • (a) Enders, D.; Breuer, K. Addition of acyl carbanion equivalents to carbonyl groups and enones. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, Germany, 1999; Vol. 3, p 1093.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 1093
    • Enders, D.1    Breuer, K.2
  • 52
    • 58049218113 scopus 로고    scopus 로고
    • Scheldt specifically states that azide does not work as a nucleophile in his enal redox chemistry; see ref 11b
    • Scheldt specifically states that azide does not work as a nucleophile in his enal redox chemistry; see ref 11b.
  • 54
    • 85177661390 scopus 로고    scopus 로고
    • Fu has recently reported asymmetric addition of hydrazoic acid to ketenes generating enantioenriched alpha-branched carbinolamines; see: Dai, X, Nakai, T, Romero, J. A. C, Fu, G. C. Angew. Chem, Int. Ed. 2007, 46, 4367
    • Fu has recently reported asymmetric addition of hydrazoic acid to ketenes generating enantioenriched alpha-branched carbinolamines; see: Dai, X.; Nakai, T.; Romero, J. A. C.; Fu, G. C. Angew. Chem., Int. Ed. 2007, 46, 4367.
  • 55
    • 33644526230 scopus 로고    scopus 로고
    • It is well established that acylazides undergo Curtius rearrangement with retention of stereochemistry. Although the acylazide is somewhat sensitive to epimerization, Lebel has shown that the azidation/Curtius/trapping sequence proceeds with predominant retention of enantioselectivity; see; Lebel, H, Leogane, O, Huard, K, Lectard, S. Pure Appl. Chem. 2006, 78, 363
    • It is well established that acylazides undergo Curtius rearrangement with retention of stereochemistry. Although the acylazide is somewhat sensitive to epimerization, Lebel has shown that the azidation/Curtius/trapping sequence proceeds with predominant retention of enantioselectivity; see; Lebel, H.; Leogane, O.; Huard, K.; Lectard, S. Pure Appl. Chem. 2006, 78, 363.
  • 56
    • 58049199815 scopus 로고    scopus 로고
    • 2 provide similar selectivity to that of ether and benzene, but with decreased yields. Acetonitrile provides only a minor amount of the desired product.
    • 2 provide similar selectivity to that of ether and benzene, but with decreased yields. Acetonitrile provides only a minor amount of the desired product.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.