Formation of enantioenriched alkanol with stochastic distribution of enantiomers in the absolute asymmetric synthesis under heterogeneous solid-vapor phase conditions

Among several theories proposed for the origin of homochirality, absolute asymmetric synthesis is unique because it produces chiral compounds without the intervention of any chiral factor. Here we report on the kinetically controlled heterogeneous solid-vapor phase absolute asymmetric synthesis in conjunction with asymmetric autocatalysis with amplification of chirality. Each reaction, carried out in a test tube, between achiral powder crystals of pyrimidine-5-carbaldehyde and the vapor of diisopropylzinc, is controlled kinetically to afford either ( S )- or ( R )-pyrimidyl alkanol. Absolute asymmetric synthesis under heterogeneous solid-vapor phase conditions in conjunction with asymmetric autocatalysis was achieved.