Abstract
Stereoselective reduction of the ketone carbonyl group in α-allyl-substituted β-keto esters with sodium tetrahydridoborate in the presence of 2 equiv of MnCl2 quantitatively afforded the corresponding syn-isomeric alcohols. The reduction of the same substrates with L-selectride [LiBH(s-Bu)3] in anhydrous THF was characterized by low chemoselectivity, and anti-isomeric alcohols were formed in about 50% yield. Under analogous conditions, α-allyl ketones smoothly reacted with L-selectride to give syn-isomeric alcohols in quantitative yield. The corresponding anti isomers were synthesized by the Mitsunobu reaction of the syn isomers with formic acid, followed by alkaline hydrolysis.
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