A new class of non-C2-symmetric ligands for oxidative and redox-neutral palladium-catalyzed asymmetric allylic alkylations of 1,3-diketones

Barry M Trost; Etienne J Donckele; David A Thaisrivongs; Maksim Osipov; James T Masters

doi:10.1021/jacs.5b00786

A new class of non-C2-symmetric ligands for oxidative and redox-neutral palladium-catalyzed asymmetric allylic alkylations of 1,3-diketones

J Am Chem Soc. 2015 Feb 25;137(7):2776-84. doi: 10.1021/jacs.5b00786. Epub 2015 Feb 16.

Authors

Barry M Trost¹, Etienne J Donckele, David A Thaisrivongs, Maksim Osipov, James T Masters

Affiliation

¹ Department of Chemistry, Stanford University , Stanford, California 94305-5080, United States.

PMID: 25629592
DOI: 10.1021/jacs.5b00786

Abstract

We report the discovery, synthesis, and application of a new class of non-C2-symmetric phosphoramidite ligands derived from pyroglutamic acid for use in both oxidative and redox-neutral palladium-catalyzed asymmetric allylic alkylations of 1,3-diketones. The resulting chiral products are typically obtained in high yield with good to excellent levels of enantioselectivity.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Alkylation
Allyl Compounds / chemistry*
Catalysis
Ketones / chemistry*
Ligands
Organophosphorus Compounds / chemistry
Oxidation-Reduction
Palladium / chemistry*
Stereoisomerism

Substances

Allyl Compounds
Ketones
Ligands
Organophosphorus Compounds
phosphoramidite
Palladium