Protecting group migration in the chemis
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StΓ©phane GΓ©rard; Jacqueline Marchand-Brynaert
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Article
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2003
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Elsevier Science
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French
β 112 KB
The alkoxide anion derived from 1-t-butyldimethylsilyl-4-hydroxymethyl-2-azetidinone (1) rearranged at -78Β°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 respective