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Volumn 128, Issue 6, 2006, Pages 2105-2114

Highly enantioselective synthesis of glycidic amides using camphor-derived sulfonium salts. Mechanism and applications in synthesis

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; LITHIUM; SALTS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 33244460806     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0568345     Document Type: Article
Times cited : (128)

References (57)
  • 17
    • 0000784042 scopus 로고
    • Fleming, I., Ed.; Pergamon Press: Oxford, U.K.
    • Rosen, T. In Comprehensive Organic Synthesis; Fleming, I., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 409.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 409
    • Rosen, T.1
  • 35
    • 33244473888 scopus 로고    scopus 로고
    • note
    • Tertiary amides were also tested but gave a mixture of regioisomers.
  • 41
    • 33244494326 scopus 로고    scopus 로고
    • note
    • Although our reaction was carried out at -50 °C rather than room temperature, we believe that temperature does not have a great effect on the enantioselectivity. Indeed, we have shown that, whereas epoxidation at -50 °C gives a product with 92% ee. the corresponding reaction at room temperature resulted in an epoxide with 87% ee (see Table 3 and ref 33).
  • 55
    • 33244475235 scopus 로고    scopus 로고
    • note
    • Calculations were carried out using the Jaguar 4.0 pseudospectral program package (Jaguar 4.0; Schrödinger, Inc.: Portland, OR, 1991-2000). Relative energies correspond to electronic energies at the indicated level of theory. See Supporting Information for computational details.
  • 57
    • 33244477303 scopus 로고    scopus 로고
    • note
    • N2 reactions. Studies aiming at understanding this dissimilarity are currently underway in our laboratories.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.