Issue 15, 2004
From the journal:

Organic & Biomolecular Chemistry

Highly enantioselective reaction of lithiated N-Boc-thiazolidine: a new chiral formyl anion equivalent

Libo Wang,a   Shuichi Nakamuraa  and  Takeshi Toru*a  

* Corresponding authors

a Department of Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, Japan
E-mail: toru@nitech.ac.jp
Fax: 81-52-735-5217
Tel: 81-52-735-5217

Abstract

Reaction of lithiated N-Boc-thiazolidine 1 with various aldehydes in the presence of (−)-sparteine afforded the products with up to 93% ee. The reaction was confirmed to proceed through a dynamic thermodynamic resolution pathway. Each diastereomeric alcohol could be converted to the corresponding optically active 1,2-ethanediols.

Graphical abstract: Highly enantioselective reaction of lithiated N-Boc-thiazolidine: a new chiral formyl anion equivalent

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Article information

DOI
https://doi.org/10.1039/B408509D
Article type
Communication
Submitted
07 Jun 2004
Accepted
24 Jun 2004
First published
08 Jul 2004

Org. Biomol. Chem., 2004,2, 2168-2169

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Highly enantioselective reaction of lithiated N-Boc-thiazolidine: a new chiral formyl anion equivalent

L. Wang, S. Nakamura and T. Toru, Org. Biomol. Chem., 2004, 2, 2168 DOI: 10.1039/B408509D

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