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Issue 17, 2017
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syn-Selective crotylation of aldehydes using bismuth-crotyl bromide-(1-butyl-3-methylimidazolium bromide) combination: some synthetic applications

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Abstract

The Bi-[bmim][Br] combination has been found to offer high syn-selectivity in the crotylation of aldehydes with crotyl bromide using practically stoichiometric amounts of the reagents. The room temperature ionic liquid (RTIL), [bmim][Br], activated Bi metal in the presence of oxygen to produce crotylbismuthdibromide, which reacted with the aldehydes at room temperature. The major antisyn diastereomeric product obtained from the crotylation of (R)-cyclohexylideneglyceraldehyde was utilized for the synthesis of dictyostatin and cryptophycin segments, and (+)-cis-aerangis lactone, using standard synthetic protocols.

Graphical abstract: syn-Selective crotylation of aldehydes using bismuth-crotyl bromide-(1-butyl-3-methylimidazolium bromide) combination: some synthetic applications

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Supplementary files

Article information


Submitted
14 Mar 2017
Accepted
07 Apr 2017
First published
07 Apr 2017

Org. Biomol. Chem., 2017,15, 3756-3774
Article type
Paper

syn-Selective crotylation of aldehydes using bismuth-crotyl bromide-(1-butyl-3-methylimidazolium bromide) combination: some synthetic applications

D. Goswami, M. R. Koli, S. Chatterjee, S. Chattopadhyay and A. Sharma, Org. Biomol. Chem., 2017, 15, 3756
DOI: 10.1039/C7OB00626H

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