Chemistry Letters, Vol.31, No.2, 168-169, 2002
Asymmetric autocatalysis of pyrimidyl alkanol induced by optically active 1,1'-binaphthyl, an atropisomeric hydrocarbon, generated from spontaneous resolution on crystallization
An atropisomeric hydrocarbon, (R)-1,1'-binaphthyl, acts as a chiral initiator of asymmetric autocatalysis of pyrimidyl alkanol in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde to afford (S)-5-pyrimidyl alkanol 2 with 96% ee. On the other hand, in the presence of (S)-1,1'-binaphthyl, the reaction affords (R)-2 with 94% ee.