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Volumn 73, Issue 7, 2008, Pages 2633-2640

A concise route to β-cyclopropyl amino acids utilizing 1,2-dioxines and stabilized phosphonate nucleophiles

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; ESTERS; NUCLEOPHILES; OXIDATION;

EID: 41649099340     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7024256     Document Type: Article
Times cited : (16)

References (52)
  • 34
    • 41649117174 scopus 로고    scopus 로고
    • A reviewer raised the point that if the cis-γ-hydroxy enones exist as the alkoxides under the basic reaction conditions then attack by the phosphonate nucleophile may occur from the opposite face to that described in Scheme 1, giving rise to intermediate A. Collapse of this intermediate via a SNi (frontside) displacement would then give rise to the cyclopropane diastereoisomer B in the opposite enantiomeric series, Chemical Equation Presented) The following scheme outlines the synthesis of cyclopropane D from trans-γ-hydroxy enone C (reaction of which proceeds via the cis γ-hydroxyenone)36 of known absolute stereochemistry. The absolute stereochemistry of cyclopropane D was established by single-crystal X-ray crystallography and supports the mechanism for cyclopropanation shown in Scheme 1 and rules out the alternative depicted above.52 Chemical Equation Presented
    • 52 (Chemical Equation Presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.