Dual catalytic enantioselective desymmetrization of allene-tethered cyclohexanones

Lin Zhang, Ken Yamazaki, Jamie A. Leitch, Ruben Manzano, Victoria A.M. Atkinson, Trevor A. Hamlin, Darren J. Dixon

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

The construction of enantioenriched azabicyclo[3.3.1]nonan-6-one heterocycles via an enantioselective desymmetrization of allene-linked cyclohexanones, enabled through a dual catalytic system, that provides synchronous activation of the cyclohexanone with a chiral prolinamide and the allene with a copper(i) co-catalyst to deliver the stereodefined bicyclic core, is described. Successful application to oxygen analogues was also achieved, thereby providing a new enantioselective synthetic entry to architecturally complex bicyclic ethereal frameworks. The mechanistic pathway and the origin of enantio- and diastereoselectivities has been uncovered using density functional theory (DFT) calculations.

Original languageEnglish
Pages (from-to)7444-7450
Number of pages7
JournalChemical Science
Volume11
Issue number28
DOIs
Publication statusPublished - Jun 28 2020
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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