Efficient Preparation of Optically Active (S)-(-)-3-Methyl-γ-butyrolactone by Catalytic Asymmetric Hydrogenation Using Chiral N-Substituted Pyrrolidinebisphosphine Rhodium Complexes

Hideo TAKEDA; Takeshi TACHINAMI; Shigeki HOSOKAWA; Masakazu ABURATANI; Kiyoshi INOGUCHI; Kazuo ACHIWA

doi:10.1248/cpb.39.2706

Hideo TAKEDA, Takeshi TACHINAMI, Shigeki HOSOKAWA, Masakazu ABURATANI, Kiyoshi INOGUCHI, Kazuo ACHIWA

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Keywords: N-substituted pyrrolidinebisphosphines ligand, asymmetric hydrogenation, rhodium-bisphosphine complex, (S)-(-)-3-methyl-γ-butyrolactone, (S)-(-)-2-methylsuccinamic acid

JOURNAL FREE ACCESS

1991 Volume 39 Issue 10 Pages 2706-2708

DOI https://doi.org/10.1248/cpb.39.2706

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Abstract

(S)-(-)-2-Methyl succinamic acid, which is a good precursor of (S)-(-)-3-methyl-γ-butyrolactone, can be prepared by homogeneous asymmetric hydrogenation of 2-methylene succinamic acid catalyzed by (2S, 4S)-N-substituted-4-(diphenylphosphino)-2-[(diphenylphosphino)-methyl]pyrrolidine-rhodium complexes. Various N-substituted pyrrolidine-bisphosphines were synthesized to find the optimum ligand for this purpose and to compare the effects of the N-substituents.

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