One-flask, regiospecific conversions of allylic alcohols into 2-carbon-extended, conjugated dienoate esters. Use of a new sulfinyl orthoester

GH Posner, RD Crouch, CM Kinter…

文献索引：Posner, Gary H.; Crouch, R. David; Kinter, Chris M.; Carry, Jean-Christophe Journal of Organic Chemistry, 1991 , vol. 56, # 25 p. 6981 - 6987

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被引用次数: 29

摘要

Sixteen differently substituted primary and secondary allylic alcohols are shown to react with sulfinyl orthoacetate 1 at 100 OC sequentially via a [3, 3] sigmatropic rearrangement and then a 8-elimination of benzenesulfenic acid to form conjugated dienoate esters 5-13 in 45- 95% yields. This one-flask, intramolecular carbon-carbon bond-forming process represents a simple and convenient method for regiospecific y-attachment of a two-carbon ( ...