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

✍ Scribed by Stéphane Gérard; Jacqueline Marchand-Brynaert

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
112 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

The alkoxide anion derived from 1-t-butyldimethylsilyl-4-hydroxymethyl-2-azetidinone (1) rearranged at -78°C 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-(phenethyloxycarbonyl) (6) derivatives of 4-(t-butyldimethylsilyloxy)methyl-2-azetidinone.

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