Tetrahedron

The reaction of trialkylvinylborates with aldehydes as applied to syntheses of 1, 3-alkanediols, 1-chloro-3-heptanol and a cyclopropane derivative

K Utimoto, K Uchida, H Nozaki

Index: Utimoto,K. et al. Tetrahedron, 1977 , vol. 33, p. 1949 - 1952

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Citation Number: 6

Abstract

Treatment of R'CHO with Li [R3BCH CH2] gives an adduct which is believed to be R2BCHR-CH2-CH (OLi) R'(2) or its borate form (3). Oxidation of the adducts with alkaline hydrogen peroxide gives ca. 1: 1 mixture of diastereomeric 1, 3-alkanediols in good yields. On the other hand, the reaction of BrMg [R3BCH CH2] with R'CHO affords less satisfactory results. Successive treatment of 2 (R= n-Bu, R'= H) with PCl5 and alkaline H2O2 gives ...

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