Stereospecific synthesis of acyclic unsaturated amino alcohols. A new approach to threo and erythro sphingosine

RS Garigipati, SM Weinreb

文献索引：Garigipati, Ravi S.; Weinreb, Steven M. Journal of the American Chemical Society, 1983 , vol. 105, # 13 p. 4499 - 4501

全文：HTML全文

被引用次数: 43

摘要

-13 R= H, R'= Me-adducts upon treatment with phenyl Grignard reagent undergo [2, 3] sigmatropic rearrangement to sulfenate esters 12 and 13, respectively, via envelope-like transition states. 8, 16 In both cases, the methyl group on the sulfur-bearing carbon (C-1) must occupy a pseudoequatorial position to avoid severe A's3 strain with substituents on C- 4. This anchor effect controls double-bond geometry