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A convenient and stereoselective conversion of aldehydes into β-bromovinyloxiranes mediated by chromium(II) chloride

✍ Scribed by Jacques Augé

Book ID: 104217719
Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 125 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)82277-7

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✦ Synopsis

The monoreduction of 1,3,3-tribromopropene by chromium(I1) chloride gave a chromium(II1) species converting aldehydes into Bbromovinyloxiranes. The stereochemistry of this new reaction is mainly temperature dependent.

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Reduction of Cp2TiC12 with s-BuMgCl in THF gave a greenish deep brown solution which has been found to promote the reductive homocoupling of aromatic and a+-unsaturated aldehydes to yield symmetrical 1,2-diols with high threo-selectivity. threo-1,2-Diols have, after resolution, frequently been utili