Diastereoselective synthesis of (-)-1-methyl-(3S,4R)-3,4-bis((2S)-N-(tert-butyloxycarbonyl)pyrrolidin-2-yl)-2-pyrrolidinone by an asymmetric Michael reaction

Mahboobi, Siavosh and Popp, Alfred and Burgemeister, Thomas and Schollmeyer, Dieter (1998) Diastereoselective synthesis of (-)-1-methyl-(3S,4R)-3,4-bis((2S)-N-(tert-butyloxycarbonyl)pyrrolidin-2-yl)-2-pyrrolidinone by an asymmetric Michael reaction. TETRAHEDRON-ASYMMETRY, 9 (13). pp. 2369-2376. ISSN 0957-4166

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Abstract

Beginning with enantiomerically pure L-proline, (-)-1-methyl-(3S,4R)-3,4-bis((2S)-N-(tert-butyloxy- carbonyl)pyrrolidin-2-yl)-2-pyrrolidinone was prepared in diastereomerically pure form. Taking advantage of the chiral induction of the L-proline derivatives, the intermolecular Michael reaction, used to build the pyrrolidinone ring, was carried out stereoselectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

Item Type: Article
Uncontrolled Keywords: CARBAZOLE DERIVATIVES; ADDITION-REACTIONS; INDUCTION
Subjects: 500 Science > 540 Chemistry & allied sciences
600 Technology > 615 Pharmacy
Divisions: Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry I (Prof. Elz)
Chemistry and Pharmacy > Institut für Organische Chemie
Depositing User: Dr. Gernot Deinzer
Date Deposited: 23 Feb 2023 11:19
Last Modified: 23 Feb 2023 11:19
URI: https://pred.uni-regensburg.de/id/eprint/49678

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