Palladium and boron co-catalyzed addition of oxygen nucleophiles to vinyl epoxides
AssigneeThe Board of Trustees of the Leland Stanford Junior University
InventorsErnest John McEachern, Francisco Dean Toste, Barry Martin Trost
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Abstract
Nucleophilic oxygen species, such as primary alcohols, carboxylates, and water, are added to vinyl epoxides in a highly regioselective and enantioselective manner, providing a convenient route to enantiomerically enriched 1,2-diols and oxygen-containing heterocycles. The reaction employs a chiral Pd(0) complex and a borane or borate as co-catalysts Also described are similar additions of nitrogen nucleophiles, and the addition of carbonates to vinyl epoxides using a chiral Pd(0) catalyst.
Claims31
A method of selectively adding a nucleophilic species to a vinylic epoxide, wherein said nucleophilic species is a nucleophilic oxygen or nitrogen species, said method comprising
- contacting said epoxide with a borane or borate reagent, in the presence of said nucleophilic species and a chiral catalytic Pd complex,
- thereby forming an addition product which is enriched in one of the possible stereoisomeric products of such addition.
A method of selectively adding carbonate to a vinylic epoxide, said method comprising contacting said epoxide, in a chlorocarbon solvent, with carbon dioxide, a carbonate, or a bicarbonate, in the presence of a chiral catalytic Pd complex and water,
- thereby forming a cyclic carbonate product which is enriched in one of the possible stereoisomeric products of such addition.
Dependencies are inferred from the claim text.