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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 17, Number 10
BKCSDE 17(10)
October 20, 1996 

 
Title
Selective Reduction of Carbonyl Compounds with Diisobutyldialkylaminoalanes
Author
Jin Soon Cha*, Sang Yong Kwon, Oh Oun Kwon, Jong Mi Kim, Hanchul Song
Keywords
Abstract
Details are described of reaction of carbonyl compounds with diisobutyldialkylaminoalane (DIBAL-NR2; R=Et, i-Bu, Ph) in order to establish their reduction characteristics. The reagents were extremely mild and reduced only aldehydes and ketones effectively in ethyl ether at 25 ℃. The stereoselectivity in the reduction of representative cyclic ketones appeared not so high but quite different from that obtained by DIBAL-H itself. The reagents reduced α,β-unsaturated aldehydes and ketones to the corresponding allylic alcohols without any detectable 1,4-reduction products. DIBAL-NR2 also achieved the selective reduction of aldehydes or ketones in the presence of keto or other readily reducible functional group, however the chemoselectivity was less satisfactory than that achieved by diisobutylethoxyalane (DI-BAL-OEt).
Page
900 - 905
Full Text
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