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US 10,745,354 B2Granted
Methods for enantioselective allylic alkylation of esters, lactones, and lactams with unactivated allylic alcohols
AssigneeCalifornia Institute of Technology
InventorsBrian M. Stoltz, Aurapat Ngamnithiporn, Carina I. Jette, Shoshana Bachman, Scott C. Virgil, Sebastian Lackner
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Abstract
The present disclosure provides methods for enantioselective synthesis of cyclic and acyclic α-quaternary carboxylic acid derivatives via nickel-catalyzed allylic alkylation.
Claims8
A method of preparing a compound of Formula (XI):
- comprising treating a compound of Formula (XII)
- in an organic solvent
- in the presence of a complex formed by contacting a Ni(0) source with a ligand,
- wherein
- PG′ is an oxygen protecting group;
- R6 is C1-5 alkyl;
- R7 is C1-5 alkyl;
- the organic solvent is toluene, diethyl ether, methyl t-butyl ether, tetrahydrofuran, or dioxane, or a mixture thereof;
- and
- the compound of Formula (XI) is enantioenriched.
7 more elements
A method of synthesizing a pharmaceutical agent, comprising preparing a compound of Formula (XI):
- the preparing comprising treating a compound of Formula (XII)
- in an organic solvent
- in the presence of a complex formed by contacting a Ni(0) source with a ligand,
- wherein
- PG′ is an oxygen protecting group;
- R6 is C1-5 alkyl;
- R7 is C1-5 alkyl;
- and
- the organic solvent is toluene, diethyl ether, methyl t-butyl ether, tetrahydrofuran, or dioxane, or a mixture thereof.
6 more elements
Dependencies are inferred from the claim text.