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The Pd-catalysed asymmetric allylic alkylation reactions of sulfamidate imines

Journal Article


Abstract


  • The Pd-catalysed asymmetric allylic alkylation (Pd-AAA) of prochiral enamide anions derived from 5H-oxathiazole 2,2-dioxides has been developed. Various 4,5-disubstituted and 4-substituted cyclic sulfamidate imines have participated in the transformation with a range of allyl carbonates - as well as 2-vinyl oxirane, 2-vinyl-N-tosylaziridine, and 2-vinyl-1,1-cyclopropane dicarboxylate - to furnish the desired C-allylated products in moderate to high yields, with high regioselectivites and generally high enantioselectivities. Conversion between N- and C-allyl products was observed, with the N-allylated products converting to the C-allylated products over time. The resulting high-value allylated heterocyclic products all bear a tetrasubstituted stereogenic centre and can be reduced to an allylated chiral sulfamidate or an amino alcohol.

Publication Date


  • 2021

Citation


  • Pham, Q. H., Tague, A. J., Richardson, C., Hyland, C. J. T., & Pyne, S. G. (2021). The Pd-catalysed asymmetric allylic alkylation reactions of sulfamidate imines. Chemical Science, 12(38), 12695-12703. doi:10.1039/d1sc03268b

Scopus Eid


  • 2-s2.0-85117092134

Start Page


  • 12695

End Page


  • 12703

Volume


  • 12

Issue


  • 38

Abstract


  • The Pd-catalysed asymmetric allylic alkylation (Pd-AAA) of prochiral enamide anions derived from 5H-oxathiazole 2,2-dioxides has been developed. Various 4,5-disubstituted and 4-substituted cyclic sulfamidate imines have participated in the transformation with a range of allyl carbonates - as well as 2-vinyl oxirane, 2-vinyl-N-tosylaziridine, and 2-vinyl-1,1-cyclopropane dicarboxylate - to furnish the desired C-allylated products in moderate to high yields, with high regioselectivites and generally high enantioselectivities. Conversion between N- and C-allyl products was observed, with the N-allylated products converting to the C-allylated products over time. The resulting high-value allylated heterocyclic products all bear a tetrasubstituted stereogenic centre and can be reduced to an allylated chiral sulfamidate or an amino alcohol.

Publication Date


  • 2021

Citation


  • Pham, Q. H., Tague, A. J., Richardson, C., Hyland, C. J. T., & Pyne, S. G. (2021). The Pd-catalysed asymmetric allylic alkylation reactions of sulfamidate imines. Chemical Science, 12(38), 12695-12703. doi:10.1039/d1sc03268b

Scopus Eid


  • 2-s2.0-85117092134

Start Page


  • 12695

End Page


  • 12703

Volume


  • 12

Issue


  • 38