Phase-Transfer Catalysed Enantioselective Epoxidation of Estra-Δ5(10),9(11)-diene Using Chiral Ammonium Salts Derived from Cinchona Alkaloids

Author(s): Ya-Xi Yang, Zheng Li, Guo-Rong Chen, Yuan-Chao Li.

Journal Name: Letters in Organic Chemistry

Volume 7 , Issue 2 , 2010

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Abstract:

A modified phase-transfer catalysed enantioselective epoxidation of estra-Δ5(10),9(11)-diene, an important intermediate of anti-early pregnancy drug mifepristone 1, have been determined and investigated. Eight chiral ammonium salts (PTC A-H), used as phase-transfer catalysts, have been synthesized from cinchona alkaloids. Among them, PTC G and PTC H have exhibited satisfying catalytic activity to improve the ratio of α/β epoxide up to 7:1.

Keywords: Mifepristone, estra-Δ5(10),9(11)-diene, cinchona alkaloids, chiral ammonium salts

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Article Details

VOLUME: 7
ISSUE: 2
Year: 2010
Page: [163 - 167]
Pages: 5
DOI: 10.2174/157017810790796237
Price: $58

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