Tetrahedron Letters p. 257 - 260 (1993)
Update date:2022-08-16
Topics:
Fuller, Joseph C.
Stangeland, Eric L.
Goralski, Christian T.
Singaram, Bakthan
Lithium 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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