Catalytic allylic alkylation
AssigneeWisconsin Alumni Research Foundation
InventorsBarry M. Trost, Thomas R. Verhoeven
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Abstract
Allylic alkylation with retention of configuration of a substrate having an allylic carbon-oxygen bond by reaction with a nucleophile in the presence of a Pd.degree. with an excess of a phosphine.
Claims15
The method in which an organic substrate having an OR group attached through the oxygen group to a carbon alpha to a double bond carbon in which OR is hydroxy, ether or ester group, comprising the displacement of the carbon-oxygen bond which is alpha to the double bond carbon and which connects to the oxygen group, with stereochemical control for retention of configuration by reacting the substrate with a nucleophile in the presence of a palladium (Pd.degree.) catalyst, in which the nucleophile is selected from the group consisting of a carbon nucleophile in the form of carbanions stabilized with at least two stabilizing groups and a nitrogen nucleophile in which the carbanion is replaced with corresponding nitrogen compounds.
The method in which an organic substrate having an OR group attached to a carbon alpha to a double bond C is substituted with a nucleophile with stereochemical control for retention of configuration by reaction of the substrate with the nucleophile in the presence of a Pd.degree. catalyst in accordance with the equation ##STR7## in which R is hydrogen or R' or OR' in which R' is an organic group and N is a nucleophile selected from the group consisting of a carbon nucleophile in the form of carbanions stabilized with at least two stabilizing groups and nitrogen nucleophiles in which the carbanions are replaced with corresponding nitrogen compounds.
Dependencies are inferred from the claim text.