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Stereoselective synthesis of 2-(S)-(3,5-bis(trifluoromethyl)benzyloxy)-3-(S)-phenyl-1,4-oxazine

✍ Scribed by Michael S. Ashwood; Ian F. Cottrell; Antony J. Davies

Publisher
Elsevier Science
Year
1997
Tongue
English
Weight
370 KB
Volume
8
Category
Article
ISSN
0957-4166

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✦ Synopsis

A convenient process for the preparation of the secondary amine 6, 2-(S)-(3,5-bis(trifluoromethyl)benzyloxy)-3-(S)-phenyl-l,4-oxazine, is described starting from the readily available (S)-phenylglycine 1. The process features efficient construction of the homochiral oxazinone intermediate 3 and stereoselective introduction of the 2-(3,5-bis(trifluoromethyl)-benzyloxy) group by L-Selectride reduction followed by in situ alkylation with the highly reactive 3,5-bis(trifluoromethyl)-benzyl triflate 4. (~) 1997 Elsevier Science Ltd. All rights reserved.

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