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Synlett 1995; 1995(10): 1027-1028
DOI: 10.1055/s-1995-5159
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A Highly Diastereoselective Epoxidation of N-Boc 2-Alkenyloxazolidines: Application in Asymmetric Synthesis

A. Agami, F. Couty* , O. Venier
  • *Laboratoire de Synthèse Asymétrique, Université P. et M. Curie, Case 47, 4 place Jussieu, 75005 Paris, France
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Publication Date:
31 December 2000 (online)

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N-Boc 2-alkenyloxazolidines derived from (R)-phenylglycinol underwent a highly diastereoselective bromocarbamoylation when treated with NBS. Reaction of the resulting bicyclic urethanes with sodium ethoxide yielded diastereomerically pure oxazolidine epoxides. This new methodology was applied to the enantioselective synthesis of the anti isomer of the taxol side chain methyl ester, i.e. (2R,3R)-N-benzoyl-3-phenylisoserine methyl ester.

oxazolidine - bromocarbamoylation - asymmetric epoxidation - taxol side chain

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