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Volumn 45, Issue 16, 2006, Pages 2617-2619

A highly enantioselective Brønsted acid catalyst for the Strecker reaction

Author keywords

Amino acids; Binol phosphate; Br nsted acids; Organocatalysis; Strecker reaction

Indexed keywords

BINOL PHOSPHATE; BRØNSTED ACIDS; ORGANOCATALYSIS; STRECKER REACTION;

EID: 33646559779     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200504344     Document Type: Article
Times cited : (200)

References (49)
  • 2
    • 0041378065 scopus 로고    scopus 로고
    • For reviews, see: a) H. Gröger, Chem. Rev. 2003, 103, 2795;
    • (2003) Chem. Rev. , vol.103 , pp. 2795
    • Gröger, H.1
  • 29
    • 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
  • 47
    • 33746299995 scopus 로고    scopus 로고
    • note
    • N-Boc-, N-tosyl-, N-phenyl-, N-benzhydryl-, and N-phosphinoyl-protected imines gave inferior results compared to the N-benzyl-protected ones. As cyanide sources we tested acetone cyanohydrine, trimethylsilyl cyanide, and HCN. Reduction of catalyst loading, temperature, and concentration resulted in loss of enantioselectivities.
  • 48
    • 33746284509 scopus 로고    scopus 로고
    • note
    • Enantioselectivities decreased in the case of aliphatic imines, for example, 2-(benzylamino)-3-methylbutane nitrile was obtained in 55% ee.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.