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

Autor:	Pham QH; School 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., Tague AJ; School 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., Richardson C; School 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., Gardiner MG; Research School of Chemistry, The Australian National University Canberra 2601 Australia., Pyne SG; School 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., Hyland CJT; School 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.
Jazyk:	angličtina
Zdroj:	Chemical science [Chem Sci] 2023 Apr 18; Vol. 14 (18), pp. 4893-4900. Date of Electronic Publication: 2023 Apr 18 (Print Publication: 2023).
DOI:	10.1039/d3sc01510f
Abstrakt:	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. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.)
Databáze:	MEDLINE
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