4.8 Article

Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 38, Pages 11651-11655

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201607053

Keywords

1,1 '-substituted olefins; allylic asymmetric substitution; allylic phosphates; dioxinones; iridium catalysis

Funding

  1. National Institutes of Health [GM-58108]

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The first Ir-catalyzed enantioselective allylation of trisubstituted allylic electrophiles has been developed. Through modification of the leaving group of allylic electrophiles, we found that trisubstituted allylic phosphates are suitable electrophiles for asymmetric allylation. The reaction of allylic phosphates with enol silanes derived from dioxinones gave allylated products in good yields with high enantioselectivities.

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