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Catalytic Enantioselective Alkylative Aldol Reaction: Efficient Multicomponent Assembly of Dialkylzincs, Allenic Esters, and Ketones toward Highly Functionalized δ-Lactones with Tetrasubstituted Chiral Centers

Kounosuke Oisaki, Dongbo Zhao, Motomu Kanai and Masakatsu Shibasaki*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0013, Japan, Email: mshibasamol.f.u-tokyo.ac.jp

K. Oisaki, D. Zhao, M. Kanai, M. Shibasaki, J. Am. Chem. Soc., 2007, 129, 7439-7443.

DOI: 10.1021/ja071512h (free Supporting Information)


Abstract

Highly functionalized δ-lactones were produced in the presence of a catalytic amount of the Cu(OAc)2-DIFLUORPHOS complex through three-component assembly of dialkylzincs, allenic esters, and unactivated ketones. This CAMCR (catalytic asymmetric multicomponent reaction) constructs two C-C bonds and one tetrasubstituted chiral center simultaneously.

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Key Words

Multicomponent Reactions, 5,6-Dihydropyran-2-ones


ID: J48-Y2007-1880