Abstract
Acid-catalyzed asymmetric allylation of 3-phenylpropanal 2a via an allyl-transfer reaction from a chiral allyl donor, (1R,2S,5R)-1-allylmenthol, gave (R)-1-phenylhex-5-en-3-ol 3b enantioselectively. The optical yield (ee) of (R)-3b, however, decreased with increasing chemical yield, and the chemical yield increased with increasing reaction time. The racemization takes place via an acid-catalyzed allyl-transfer reaction from (R)-3b to 2a.
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