Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 24, Pages 9521-9526Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b04658
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Funding
- Tamaki Foundation
- Bing Summer Undergraduate Fellowship
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We describe the development of a Pd-catalyzed asymmetric allylic alkylation (Pd-AAA) of acyclic alpha-hydroxyketones using boronic acids as traceless templates. Condensation of boronic acids with hydroxyketones generates 1,3-dioxaboroles, which can be used directly as pronucleophiles in Pd-AAA reactions. This strategy enables control of the enolate geometry, while removing the issue of O-alkylation. Allylic alcohols can be directly ionized in the presence of Pd(0) and chiral ligands to afford alkylation products with regio- and enantioselectivity. Additionally, a dynamic kinetic asymmetric transformation of allenyl electrophiles affords C-alkylation products in high regio-, diastereo-, and enantioselectivity. To the best of our knowledge, this method represents the first example in Pd-AAA for setting point chirality on a nucleophile simultaneous to stereoinduction on an axial chiral allene.
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