The Journal of Organic Chemistry

Homologation of carbonyl compounds to aldehydes with lithium bis (ethylenedioxyboryl) methide

DS Matteson, RJ Moody

文献索引：Matteson, Donald S.; Moody, Robert J. Journal of Organic Chemistry, 1980 , vol. 45, # 6 p. 1091 - 1095

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被引用次数: 57

摘要

Tris (ethylenedioxybory1) methane reacts with methyllithium at-78" C in THF to form lithium bis (ethy1-enedioxyboryl) methide, which reacts with aldehydes and ketones to form 1- alkene-1-boronic esters. These need not be isolated for efficient oxidation by sodium perborate to the homologated aldehydes, which are easily purified. Systematic investigation of the reaction conditions to optimize yields at each step was undertaken. Possibly ...