Stereocontrolled Synthesis of N-Vinyl-, N-(1'-Propenyl)-, and N-Unsubstituted-β-lactams from 2-Aza-1,3-butadienes via the Staudinger Reaction
2-Aza-1,3-butadienes 2 and 5 were synthesized in good yields and on a large scale.Reaction of 2 and 5 with acid chlorides in the presence of triethylamine (Staudinger reaction) resulted in the high-yielding formation of N-vinyl- and N-(1'-propenyl)-β-lact
N-vinyl and N-unsubstituted β-lactams from 1-substituted 2-aza-1,3-butadienes
The reaction of acid chlorides and N-vinyl imines results in the stereoselective formation of cis N-vinyl β-lactams. The N-vinyl protecting group can be removed either oxidatively or hydrolytically to yield N-substituted β-lactams.
Georg,He,Kant,Mudd
p. 451 - 454
(2007/10/02)
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