Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 55, No. 2, 2001, pp.353-364
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9114
A Three-Step Synthesis of Optically ActiveÅ@5-Halomethyl-2-oxazolidinones; Asymmetric Desymmetrization of Prochiral 1,3-Dihalo-2-propyl Carbamates

Shigeo Sugiyama, Kenji Morishita, and Keitaro Ishii*

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

Optically active 5-bromomethyl-2-oxazolidinones (2a and 3a) and 5-Å@chloromethyl-2-oxazolidinones (2b and 3b) were readily prepared from prochiral 1,3-dibromo-2-propanol (7a) and 1,3-dichloro-2-propanol (7b) by a three-step sequence involving formation of carbamates (6a-c) followed by asymmetric desymmetrization (up to 50% de) and debenzylation by anisole-methanesulfonic acid system.