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Diastereoselective arylation of l-proline derivatives at the 5-position

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Title: Diastereoselective arylation of l-proline derivatives at the 5-position
Authors: Onomura, Osamu / Kirira, Peter G / Tanaka, Toshimitsu / Tsukada, Shinsuke / Matsumura, Yoshihiro / Demizu, Yosuke
Issue Date: 4-Aug-2008
Publisher: Elsevier BV
Citation: Tetrahedron, 64(32), pp.7498-7503; 2008
Abstract: Diastereoselective introduction of nucleophiles into L-proline derivatives at the 5-position was achieved with suitable selection of N-protecting group. N-Methoxycarbonylated or benzyloxycarbonylated L-proline derivatives reacted with arene to give cis-arylated products. On the other hand, N-benzoylated L-proline derivative preferentially gave trans-arylated product which could be easily transformed into optically active C2-symmetrical pyrrolidine derivative. Such derivative 5, worked well as an organic activator in the asymmetric reduction of aromatic imines by Cl3SiH.
Keywords: Diastereoselective / Organocatalysis / Asymmetric reduction of imines / C2-Symmetrical pyrrolidine / Proline derivative
URI: http://hdl.handle.net/10069/18699
ISSN: 00404020
DOI: 10.1016/j.tet.2008.06.004
Rights: Copyright (c) 2008 Elsevier Ltd All rights reserved.
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/18699

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