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 journalArticle

48 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
Publication statusPublished - 1994

Fingerprint

Lactams
Imines
Cycloaddition
Palladium
Carbonylation
Carbon Monoxide
Carboxylic Acids
Ketones
Amines
Esters
Phosphates
Derivatives
Temperature

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Palladium-catalyzed carbonylative [2 + 2] cycloaddition for the stereoselective synthesis of either cis- or trans-3-alkenyl β-lactams. / Tanaka, Hideo; Hai, A. K M Abdul; Sadakane, Masahiro; Okumoto, Hiroshi; Torii, Sigeru.

In: Journal of Organic Chemistry, Vol. 59, No. 11, 1994, p. 3040-3046.

Research output: Contribution to journalArticle

Tanaka, Hideo ; Hai, A. K M Abdul ; Sadakane, Masahiro ; Okumoto, Hiroshi ; Torii, Sigeru. / Palladium-catalyzed carbonylative [2 + 2] cycloaddition for the stereoselective synthesis of either cis- or trans-3-alkenyl β-lactams. In: Journal of Organic Chemistry. 1994 ; Vol. 59, No. 11. pp. 3040-3046.
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