A highly enantioselective synthesis of chiral allylic alcohols by asymmetric addition of novel mixed reagents of trialkenylbismuthines/dialkylzincs to aldehydes

A novel mixture of reagents of trialkenylbismuthines/dialkylzincs was developed and applied toward the synthesis of chiral allylic alcohols. The chiral β-amino alcohols catalyzed addition of the mixed reagents of trialkenylbismuthines/dialkylzincs to aldehydes gave enantiomerically enriched allylic alcohols with up to 97% ee.

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(R)-1-(4-Bromophenyl)prop-2-en-1-olC9H9BrOEe = 97%[α]D22=-16.8 (c 1.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(R)-1-(4-Bromophenyl)-2-methylprop-2-en-1-olC10H11BrOEe = 94%[α]D22=+13.9 (c 1.8, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(R)-1-(Naphthalene-2-yl)-2-methylprop-2-en-1-olC14H14OEe = 92%[α]D22=+17.6 (c 2.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(R)-1-(4-Bromophenyl)-3-methylbut-2-en-1-olC11H13BrOEe = 80%[α]D22=-89.4 (c 1.3, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)