Tetrahedron

Enantioselective construction of nitrogen-substituted quaternary carbon centers adjacent to the carbonyl group in the cyclohexane ring: first asymmetric synthesis of …

R Yokoyama, S Matsumoto, S Nomura, T Higaki…

Index: Yokoyama, Reiko; Matsumoto, Satoshi; Nomura, Satoshi; Higaki, Takafumi; Yokoyama, Takeshi; Kiyooka, Syun-ichi Tetrahedron, 2009 , vol. 65, # 27 p. 5181 - 5191

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Citation Number: 18

Abstract

Enantioselective construction of nitrogen-substituted quaternary carbon centers adjacent to the carbonyl group in the cyclohexane ring was performed with respect to the asymmetric synthesis of anesthetic (S)-ketamine 1. Diastereoselective nucleophilic 1, 2-addition reaction of phenyllithium to α-ketoxime-ether acetal 9 bearing chiral auxiliary on the α-carbonyl function gave benzyloxyamine 11 major in 83% yield with 82% de, which was converted ...