Stereocontrolled Synthesis of N-Vinyl-, N-(1'-Propenyl)-, and N-Unsubstituted-β-lactams from 2-Aza-1,3-butadienes via the Staudinger Reaction

Gunda I. Georg, Ping He, Joydeep Kant, Zhi jun Wu

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Abstract

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-(l'-propenyl)-β-lactams. Excellent cis-stereoselectivity was observed in the reaction of 2-aza-1,3-butadienes 2 and 5 with Bose-Evans ketenes and Sheehan ketenes, whereas reaction with a Moore ketene gave, as expected, a trans β-lactam. N-Formyl, N-vinyl, and N-(l'-propenyl) groups at the β-lactam nitrogen could be cleaved oxidatively in one step and in good yields by treatment with potassium permanganate. It was also found that the N-vinyl group can be removed successfully under hydrolytic conditions to yield N-unsubstituted-β-lactams.

Original languageEnglish (US)
Pages (from-to)5771-5778
Number of pages8
JournalJournal of Organic Chemistry
Volume58
Issue number21
DOIs
StatePublished - Jan 1 1993
Externally publishedYes

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