American Chemical Society
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A Novel Class of Nonbiaryl Atropisomeric P,O-Ligands for Palladium-Catalyzed Asymmetric Allylic Alkylation

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posted on 2002-04-03, 00:00 authored by Wei-Min Dai, Kelly Ka Yim Yeung, Jin-Teng Liu, Ye Zhang, Ian D. Williams
A novel class of nonbiaryl atropisomeric P,O-ligands possessing an N,N-dialkyl-1-naphthamide skeleton has been synthesized via an efficient chemical resolution process. It represents the first example of axially chiral P,O-ligands devoid of central chirality. Up to 94.7% ee was obtained for the Pd-catalyzed asymmetric allylic alkylation (AAA). Effects of solvent, base, and the bulk of the C8 oxygen group of the P,O-ligand on the AAA reaction were examined.