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A Three-Step General Synthesis of 2-Azetidinones Bearing N-Dehydroamino Acid Side Chains (1998)

Alcaide, Benito ; Polanco, Concepción ; Sierra, Miguel A.

Weinheim : Wiley-Blackwell

Liebigs Annalen 1998 (1998), S. 2913-2921

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ISSN: 1434-193X

Keywords: Lactams ; Asymmetric synthesis ; N-Vinyl-2-azetidinones ; Cyclizations ; Polycyclic 2-azetidinones ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: An efficient, three-step synthesis of N-vinyl-2-azetidinones 7 starting from α- or β-amino ester imines 3 has been developed. Staudinger reaction between imines 3 and a ketene precursor gave 2-azetidinones 4. Enolate formation on the amino ester moiety of the 2-azetidinone 4, selenation, and finally m-CPBA treatment, afforded N-vinyl-2-azetidinones 7 in fair to excellent yields, with total retention of the stereochemistry of the starting material. Two examples of the use of compounds 7 in preparing bi- and tricyclic 2-azetidinones are presented.

Type of Medium: Electronic Resource

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