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Paper | Regular issue | Vol 87, No. 2, 2013, pp.329-340
Published online, 6th December, 2012
DOI: 10.3987/COM-12-12624
Kinetic Resolution of Secondary Alcohols by Chiral DMAP Derivatives Prepared by the Ugi Multicomponent Reaction

Hiroki Mandai,* Shunsuke Irie, Masaru Akehi, Kazunobu Yuri, Masaaki Yoden, Koichi Mitsudo, and Seiji Suga*

*Division of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan

Abstract

The kinetic resolution of secondary alcohols was examined by new chiral DMAP derivatives, which can readily be prepared by the Ugi multicomponent reaction in a one-pot operation. The initial screening of DMAP derivatives indicated that the catalyst bearing L-valine with an S configuration at the α-position of amide showed the best stereoselectivity factor. After the reaction conditions were optimized with (S,S)-4a in the kinetic resolution of secondary alcohols, various acyclic and cyclic secondary alcohols could be resolved with an s-factor of up to 12.