Redox Isomerization/(3+2) Allenoate Annulation by Auto-Tandem Phosphine Catalysis

Jeremy T. Maddigan-Wyatt, Mitchell T. Blyth, Jhi Ametovski, Michelle L. Coote, Joel F. Hooper, David W. Lupton

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

A phosphine-catalyzed approach to pyrrolines has been developed that involves two mechanistically unlinked catalytic processes. The first involves the redox isomerization of amino crotonates to provide access to aliphatic tosyl imines, which then engage in a (3+2) annulation with various allenoates. The reaction shows generality, with 24 examples established, along with a low yielding and moderately enantioselective variant. Mechanistic studies indicate that the viability of the process is linked to the selection of catalysts with similar propensity to add to the two coupling partners.

Original languageEnglish
Pages (from-to)16232-16236
Number of pages5
JournalChemistry - A European Journal
Volume27
Issue number65
DOIs
Publication statusPublished - 22 Nov 2021
Externally publishedYes

Bibliographical note

Funding Information:
The authors thank the Australian Research Council through the Discovery (DP200101448) and Laureate (FL170100041) programs for financial support, and the National Computational Infrastructure for supercomputing time.

Publisher Copyright:
© 2021 Wiley-VCH GmbH

Keywords

  • annulation
  • phosphine catalysis
  • redox isomerization
  • tandem catalysis

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