Palladium-catalysed enantio- and regioselective (3 + 2) cycloaddition reactions of sulfamidate imine-derived 1-azadienes towards spirocyclic cyclopentanes.

Quoc Hoang Pham, Andrew J Tague, Christopher Richardson, Michael G Gardiner, Stephen G Pyne, Christopher J T Hyland

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Article in Chemical science, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 · Who and what money

Authors and funding

6 authors.

Quoc Hoang PhamSchool of Chemistry and Molecular Bioscience, Molecular Horizons Research Institute, University of Wollongong Wollongong 2522 New South Wales Australia chrhyl@uow.edu.au spyne@uow.edu.au.ORCID https://orcid.org/0000-0002-0503-1151

Andrew J TagueSchool of Chemistry and Molecular Bioscience, Molecular Horizons Research Institute, University of Wollongong Wollongong 2522 New South Wales Australia chrhyl@uow.edu.au spyne@uow.edu.au.ORCID https://orcid.org/0000-0003-0561-4629

Christopher RichardsonSchool of Chemistry and Molecular Bioscience, Molecular Horizons Research Institute, University of Wollongong Wollongong 2522 New South Wales Australia chrhyl@uow.edu.au spyne@uow.edu.au.ORCID https://orcid.org/0000-0002-5804-6322

Michael G GardinerResearch School of Chemistry, The Australian National University Canberra 2601 Australia.ORCID https://orcid.org/0000-0001-6373-4253

Stephen G PyneSchool of Chemistry and Molecular Bioscience, Molecular Horizons Research Institute, University of Wollongong Wollongong 2522 New South Wales Australia chrhyl@uow.edu.au spyne@uow.edu.au.ORCID https://orcid.org/0000-0003-0462-0277

Christopher J T HylandSchool of Chemistry and Molecular Bioscience, Molecular Horizons Research Institute, University of Wollongong Wollongong 2522 New South Wales Australia chrhyl@uow.edu.au spyne@uow.edu.au.ORCID https://orcid.org/0000-0002-9963-5924

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

An enantio- and diastereoselective Pd-catalysed (3 + 2) cycloaddition of bis(trifluoroethyl) 2-vinyl-cyclopropane-1,1-dicarboxylate (VCP) with cyclic sulfamidate imine-derived 1-azadienes (SDAs) has been developed. These reactions provide highly functionalized spiroheterocycles having three contiguous stereocentres, including a tetrasubstituted carbon bearing an oxygen functionality. The two geminal trifluoroethyl ester moieties can be manipulated in a facially selective manner to afford more diversely decorated spirocycles with four contiguous stereocentres. In addition, diastereoselective reduction of the imine moiety can also afford a fourth stereocentre and exposes the important 1,2-amino alcohol functionality.

Identifiers

PMID37181759

DOI10.1039/d3sc01510f

PMCPMC10171190

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