Protecting group migration in the chemistry of 1-t-butyldimethylsilyl-4-hydroxymethyl-2-azetidinone

Gerard, Sabine;Marchand-Brynaert, Jacqueline
(2003) Tetrahedron Letters — Vol. 44, n° 33, p. 6339-6342 (2003)

Files

pdfdocument.pdf
  • Restricted Access
  • Adobe PDF
  • 111.96 KB
Request a copy

Details

Authors
  • Gerard, SabineUCLouvain
    Author
  • Marchand-Brynaert, JacquelineUCLouvain
    Author
Abstract
The alkoxide anion derived from 1-t-butyldimethylsilyl-4-hydroxymethyl-2-azetidinone (1) rearranged at -78degreesC into amide anion by N-O migration of the silyl protecting group. The occurrence of this intermediate was proved by quenching with benzyl bromide and phenethyl chloroformate, giving respectively N-benzyl (4) and N-(phenethyloxycarborlyl) (6) derivatives of 4-(t-butyldimethylsilyloxy)methyl-2-azetidinone. (C) 2003 Elsevier Ltd. All rights reserved.
Affiliations

Citations

  • APA
  • Chicago
  • FWB

Gerard, S., & Marchand-Brynaert, J. (2003). Protecting group migration in the chemistry of 1-t-butyldimethylsilyl-4-hydroxymethyl-2-azetidinone. Tetrahedron Letters, 44(33), 6339-6342. https://doi.org/10.1016/S0040-4039(03)01525-9 (Original work published 2003)