From vicinal azido alcohols to Boc-amino alcohols or oxazolidinones, with trimethylphosphine and Boc 2 O or CO 2

X Ariza, O Pineda, F Urpı́, J Vilarrasa

Index: Ariza, Xavier; Pineda, Oriol; Urpi, Felix; Vilarrasa, Jaume Tetrahedron Letters, 2001 , vol. 42, # 30 p. 4995 - 4999

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Citation Number: 35

Abstract

A practical solution to the problem of converting directly 1, 2-azido alcohols to Boc-amino alcohols, without recourse to catalytic hydrogenation, involves the use of Me3P/Boc2O in THF (or CH2Cl2) and aqueous NaOH at rt (90–98% yields). The same azido alcohols can be converted in one-pot to the corresponding oxazolidinones with Boc2O/DMAP/Me3P or even better with CO2 and Me3P under basic catalysis (91–96% yields).