Aminoborohydrides. 2. Regiospecific reductions of α, β-unsaturated carbonyl compounds with lithium pyrrolidinoborohydride. A facile conversion of α, β-unsaturated aldehydes and ketones to the corresponding allylic alcohols in high purity
1993; Elsevier BV; Volume: 34; Issue: 2 Linguagem: Inglês
10.1016/s0040-4039(00)60561-0
ISSN1873-3581
AutoresJoseph C. Fuller, Eric L. Stangeland, Christian T. Goralski, Bakthan Singaram,
Tópico(s)Advanced Synthetic Organic Chemistry
ResumoLithium aminoborohydrides (LiABH3), obtained by the reaction of n-BuLi with amine-boranes, are powerful reducing agents for the reduction α, β-unsaturated aldehydes and ketones to the corresponding allylic alcohols. Thus, lithium pyrrolidinoborohydride (LiPyrrBH3) and reduces cinnamaldehyde and cyclohexenone to give exclusively cinnamyl alcohol and 2-cyclohexen-1-ol respectively. This 1, 2-reduction appears to be general and ester groups are tolerated. The yield of allylic alcohols from this procedure is essentially quantitative.
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