Tetrahedron p. 1937 - 1942 (1980)
Update date:2022-08-29
Topics:
Loupy, Andre
Seyden-Penne, Jacqueline
A reversal of regioselectivity of LiAlH4 or LiBH4 reduction of 2-cyclohexenone induced by addition of <2.1.1>-cryptand to the reaction medium is accompanied by a rate decrease.In the absence of the cryptand, carbonyl attack predominates (C1:C3=86:14 with LiAlH4 in THF).In the presence of the cryptand, double bond attack is favoured (C1:C3=14:86).This effect is larger with LiAlH4 than with LiBH4.This trend is general in the case of five substituted 2-cyclohexenones.Using 12-crown-4 as a Li+ coordinator, a change in regioselectivity occurs but it is less pronunced than with the cryptand.
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