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*

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

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. This journal is

Original languageEnglish
Pages (from-to)7444-7450
Number of pages7
JournalChemical Science
Volume11
Issue number28
Early online date24 Jun 2020
DOIs
Publication statusPublished - 28 Jun 2020

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