The Pd-catalysed asymmetric allylic alkylation (Pd-AAA) of prochiral enamide anions derived from 5-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--tosylaziridine, and 2-vinyl-1,1-cyclopropane dicarboxylate-to furnish the desired -allylated products in moderate to high yields, with high regioselectivites and generally high enantioselectivities. Conversion between - and -allyl products was observed, with the -allylated products converting to the -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.
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| http://dx.doi.org/10.1039/d1sc03268b | DOI Listing |
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