Hydrolysis of substituted 1,3,2-dioxaborolanes and an asymmetric synthesis of a differentially protected syn,syn-3-methyl-2,4-hexanediol

Journal Article · Fri Aug 23 00:00:00 EDT 1996 · Journal of Organic Chemistry

DOI:https://doi.org/10.1021/jo960684m· OSTI ID:494148

Matteson, D S; Man, Hon-Wah ^[1]

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1. Washington State Univ., Pullman, WA (United States)

Pinanediol boronic esters have been cleaved only by destruction of the pinanediol with boron trichloride, reduction to borohydride with lithium aluminum hydride, or conversion to a boronic ester, or, if the boronic acid is water soluble, transesterification with phenylboronic acid in a two-phase system. The method of hydrolysis reported in this note appears to be generally useful for boronic esters of C{sub 2}-symmetrical diols but falls short of complete hydrolysis of pinanediol esters. 18 refs., 1 tab.

• OSTI ID: 494148
• Journal Information: Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 17 Vol. 61; ISSN JOCEAH; ISSN 0022-3263
• Country of Publication: United States
• Language: English

Related Subjects

40 CHEMISTRY
CHEMICAL PREPARATION
GLYCOLS
HYDROLYSIS
ORGANIC BORON COMPOUNDS
REDUCTION