Chemoenzymatic synthesis of (3R,4S)- and (3S,4R)-3-methoxy-4-methylaminopyrrolidine

Ahmed Kamal; Ahmad Ali Shaik; Mahendra Sandbhor; M. Shaheer Malik; Shaik Azeeza

doi:10.1016/j.tetasy.2006.10.031

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Chemoenzymatic synthesis of (3R,4S)- and (3S,4R)-3-methoxy-4-methylaminopyrrolidine

Journal article

Peer reviewed

Chemoenzymatic synthesis of (3R,4S)- and (3S,4R)-3-methoxy-4-methylaminopyrrolidine

Ahmed Kamal, Ahmad Ali Shaik, Mahendra Sandbhor, M. Shaheer Malik and Shaik Azeeza

Tetrahedron: asymmetry, Vol.17(20), pp.2876-2883

06/11/2006

DOI: https://doi.org/10.1016/j.tetasy.2006.10.031

Abstract

Chemistry

Chemistry, Inorganic & Nuclear

Chemistry, Organic

Chemistry, Physical

Physical Sciences

Science & Technology

An efficient and a convenient enantio selective synthesis of (3R,4S)-3-methoxy-4-methylaminopyrrolidine has been carried out by a lipase-mediated resolution protocol. This method describes the preparation of (+/-)-l-Cbz-cis-3-azido-4-hydroxypyrrolidine starting from commercially available diallylamine followed by ring-closing metathesis (RCM) via S(N)2 displacement reactions. Pseudomonas cepacia lipase immobilized on diatomaceous earth (Amano PS-D) provides (3R,4S)-11 and (3S,4R)-12 in an excellent enantiomeric excess. (c) 2006 Elsevier Ltd. All rights reserved.

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Title: Chemoenzymatic synthesis of (3R,4S)- and (3S,4R)-3-methoxy-4-methylaminopyrrolidine
Creators - without role: Ahmed Kamal
Ahmad Ali Shaik
Mahendra Sandbhor
M. Shaheer Malik
Shaik Azeeza
Publication Details: Tetrahedron: asymmetry, Vol.17(20), pp.2876-2883
Publisher: Elsevier
Number of pages: 8
Identifiers: 9931422208331
Academic Unit: Umm Al Qura University
Language: English
Resource Type: Journal article