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Paper | Special issue | Vol 44, No. 1, 1997, pp.443-457
Published online:
DOI: 10.3987/COM-96-S43
Novel Synthesis of Heterocycles Using Nickel(0)-catalyzed [2+2+2] Cocyclization: Catalytic Asymmetric Synthesis of Isoindoline and Isoquinoline Derivatives

Yoshihiro Sato, Toyoki Nishimata, and Miwako Mori*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan

Abstract

A nickel(0)-catalyzed asymmetric [2+2+2] cocyclization has been realized for the first time. That involves conceptually new enantiotopic group selective formation of the nickelacyclopentadiene (18) and produces the isoindoline (26a) (73% ee, 78% conv. yield) and isoquinoliie (27b) (54% ee, 62% yield) having benzylic chiral carbon centers.

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