Palladium-Catalyzed Carbonylative [2 + 2] Cycloaddition for the Stereoselective Synthesis of Either cis- or trans-3-Alkenyl β-Lactams

Hideo Tanaka, A. K.M.Abdul Hai, Masahiro Sadakane, Hiroshi Okumoto, Sigeru Torii

Research output: Contribution to journalArticlepeer-review

49 Citations (Scopus)

Abstract

A new potential alkenylketene equivalent, prepared without use of a carboxylic acid or an activated derivative, has been exploited. Palladium-catalyzed carbonylation of an allyl phosphate in the presence of an imine and a tertiary amine under CO pressure (30 kg cm−2) stereoselectively gave either a cis- or trans-3-alkenyl β-lactam in high yield. The stereochemical outcome strongly depends on the nature of the imine employed. Imines conjugated with a carbonyl such as a ketone or an ester stereoselectively produce cis-β-lactams at room temperature, whereas imines unconjugated with a carbonyl group exclusively afford trans-β-lactams at 70 °C.

Original languageEnglish
Pages (from-to)3040-3046
Number of pages7
JournalJournal of Organic Chemistry
Volume59
Issue number11
DOIs
Publication statusPublished - Jun 1 1994

ASJC Scopus subject areas

  • Organic Chemistry

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