Stereospecific rearrangement of β-amino alcohols catalyzed by H2SO4

TX Métro, DG Pardo, J Cossy

Index: Metro, Thomas-Xavier; Pardo, Domingo Gomez; Cossy, Janine Synlett, 2007 , # 18 p. 2888 - 2890

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Citation Number: 2

Abstract

Highly enantioselective rearrangement of β-amino alcohols was realized by using a catalytic amount of H 2 SO 4 . ... N,N-Dialkyl-β-amino alcohols can rearrange via an aziridinium intermediate when treated with SOCl 2 , [1] SOBr 2 , [2] MsCl, [3] TsCl, [3c] CBr 4 /PPh 3 , [4] Ph 3 PCl 2 , [5] Ph 3 PBr 2 , [5] DEAD/PPh 3 , [3b] [6] Ms 2 O, [3b] Tf 2 O, [7] DAST, [8] or Deoxofluor ® . [9] We have previously shown that N,N-dialkyl-β-amino alcohols of type B could be obtained ...