Title

The Pd-catalysed asymmetric allylic alkylation reactions of sulfamidate imines

Publication Name

Chemical Science

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.

Open Access Status

This publication may be available as open access

Volume

12

Issue

38

First Page

12695

Last Page

12703

Funding Number

DP180101332

Funding Sponsor

Australian Research Council

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Link to publisher version (DOI)

http://dx.doi.org/10.1039/d1sc03268b