Stereochemical Studies. X. Effects of Neighboring Functional Groups on 1,2-Asymmetric Induction in the Reduction of Propiophenone Derivatives with Sodium Borohydride

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概要

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• Effects of neighboring functional groups on 1,2-asymmetric induction in sodium borohydride reduction were examined with eight kinds of ketones (I-VIII) having functional groups, such as-NH_2HCl, -OH, and -OCH_3,at α-and/or β-positions to the carbonyl group. It was recognized that the stereochemical course of the reduction was highly dependent on the position of these functional groups, i.e. erythro-rich products were obtained in reduction of ketones having a functional group at α-position to the carbonyl group, while threo-rich products were obtained in reduction of ketones having a functional group at β-position to the carbonyl group. A six-membered empirical model (XXXVII) was proposed for predicting the stereochemical course in the reduction of ketones having a functional group at β-position to the carbonyl group. Determinations of the relative configurations of the diastereomers (X, XI, XII, XIV, XV, and XVI) were also performed.

• 公益社団法人日本薬学会の論文
• 1972-03-25

著者

• 古賀 憲司

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 山田 俊一

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• Koga Kenjiro

  Department Of Pharmaceutics Faculty Of Pharmaceutical Sciences Hokuriku University

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