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Paper | Regular issue | Vol 53, No. 10, 2000, pp.2183-2189
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8979
Catalytic Asymmetric Synthesis and Asymmetric Autocatalysis of Chiral 5,5’-(3,3’-Bipyridyl)dialkanediol

Shigehisa Tanji, Tomohiko Nakao, Itaru Sato, and Kenso Soai*

*Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Kagurazaka, Shinjuku-ku, Tokyo, 162-8601 Japan

Abstract

(S,S)-(-)-5,5′-(3,3′-Bipyridyl)dialkanediols (5a, b) with up to 98.6% e.e. was synthesized by the enantioselective addition of dialkylzincs to 3,3′-bipyridine-5,5′-dicarbaldehyde (4) using N,N-dipropylnorephedrine as a chiral catalyst. Chiral diol (5a) was found to work as an asymmetric autocatalyst in the enantioselective addition of diisopropylzinc to aldehyde (4).