Tetrahedron

A practical synthesis of optically active aromatic epoxides via asymmetric transfer hydrogenation of α-chlorinated ketones with chiral rhodium–diamine catalyst

T Hamada, T Torii, K Izawa, T Ikariya

Index: Hamada, Takayuki; Torii, Takayoshi; Izawa, Kunisuke; Ikariya, Takao Tetrahedron, 2004 , vol. 60, # 34 p. 7411 - 7417

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Citation Number: 81

Abstract

A practical method for the synthesis of optically active aromatic epoxides has been developed via the formation of optically active α-chlorinated alcohols and intramolecular etherification. Optically active alcohols with up to 99% ee can be obtained from the asymmetric reduction of aromatic ketones with a substrate/catalyst ratio of 1000–5000 using a formic acid/triethylamine mixture containing a well-defined chiral Rh complex, Cp* RhCl ...