Journal of the American Chemical Society

Organoboranes. 32. Homologation of alkylboronic esters with methoxy (phenylthio) methyllithium: regio-and stereocontrolled aldehyde synthesis from olefins via …

HC Brown, T Imai

文献索引：Brown; Imai Journal of the American Chemical Society, 1983 , vol. 105, # 20 p. 6285 - 6289

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被引用次数: 41

摘要

Abstract: Homologation of 2-alkyl-l, 3, 2-dioxaborinanes, RB02C3H6 (l), to a-methoxyalkyl derivatives, RCH (OMe) B02C3H6 (2), was achieved by reaction with LiCH (OMe) SPh, followed by treatment with HgC1,. The intermediates 2 were smoothly oxidized with hydrogen peroxide in a pH 8 phosphate buffer to give the corresponding aldehydes, RCHO (3). The alkyl groups of 1 were introduced by the hydroboration method. Thus, heptanal, 3- ...