Convenient Procedures for the Asymmetric Reduction of 1,4-Diphenylbutane-1,4-dione and Synthesis of 2,5-Diphenylpyrrolidine Derivatives

Mariappan Periasamy; Muthu Seenivasaperumal; Vutukuri Dharma Rao

doi:10.1055/s-2003-42447

PAPER

Convenient Procedures for the Asymmetric Reduction of 1,4-Diphenylbutane-1,4-dione and Synthesis of 2,5-Diphenylpyrrolidine Derivatives

Mariappan Periasamy*, Muthu Seenivasaperumal, Vutukuri Dharma Rao
School of chemistry, University of Hyderabad, Hyderabad 500 046, India
Fax: +91(40)23012460; e-Mail: mpsc@uohyd.ernet.in;

Abstract

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Abstract

Asymmetric reduction of 1,4-diphenylbutane-1,4-dione (1) was carried out using the reducing agents NaBH₄, BH₃·THF, and PhΝEt₂·ΒΗ₃ in combination with the chiral reagents (S)-(-)-α,α-diphenyl-2-pyrrolidinemethanol (4) or (S)-proline (5), in the presence of TMSCl or B(OMe)₃ under various conditions to obtain the corresponding 1,4-diol 2 in 52% to 97% ee. The chiral 1,4-diol 2 was converted to various C₂-symmetric (2S,5S)-2,5-diphenylpyrrolidine derivatives 3a-e (45 to 75% yield) via the corresponding dimesylate prepared using MsCl and Et₃N.

Key words

asymmetric reduction - chiral 1,4-diols - chiral pyrrolidine derivatives - 1,4-dione

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