Tetrahedron Asymmetry p. 957 - 963 (1997)
Update date:2022-07-29
Topics:
Ashwood, Michael S.
Cottrell, Ian F.
Davies, Antony J.
A convenient process for the preparation of the secondary amine 6, 2-(S)-(3,5-bis(trifluoromethyl)benzyloxy)-3-(S)- (3,5-bis(trifluoromethyl)benzyloxy)-3-(S)-phenyl-1,4-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.
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