Chem. Pharm. Bull., 48(2),306-307, February 2000

Communications to the Editor

One-pot Enantioselective Synthesis of Optically Active Homoallylic Alcohols from Allyl Halides


Makoto NAKAJIMA,* Makoto SAITO, and Shunichi HASHIMOTO

Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-12 Nishi-6, Kita-ku, Sapporo 060-0812, Japan.

A one-pot, convenient method for the preparation of optically active homoallylic alcohols from allyl halides was developed. Allyltrichlorosilanes were generated in situ from allyl halides and trichlorosilane in the presence of cuprous chloride and tertiary amine. Without isolation of the allyltrichlorosilanes, benzaldehyde and chiral biquinoline N, N'-dioxide were introduced into the same flask, producing the corresponding homoallylic alcohols with good to high enantioselectivities.

Key words one-pot synthesis; homoallylic alcohol; N-oxide; enantioselective allylation; chiral catalyst