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Updated: Jan 27, 2026

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
Published on: January 17, 2020
Access to Chiral Tertiary α-Hydroxyesters via Rhodium-Catalyzed Enantioselective Allylation of α-Ketoesters
Yu-Chu Yang1, Wei-Sian Li1, Tsung-Ying Uang1
1Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan.
Abstract:
Molecules containing a tertiary α-hydroxy carbonyl moiety are vital building blocks for synthesizing pharmaceuticals and natural products. In this study, we present an efficient rhodium(I)-catalyzed enantioselective allylation of α-ketoesters, providing a direct route to tertiary α-hydroxy esters. Operating at 5 °C, the method employs various α-ketoesters and allylBpin reagents to deliver the enantiomerically enriched tertiary homoallylic α-hydroxyesters bearing quaternary centers in high yields (up to 99%), excellent enantioselectivity (up to 98% ee), and diastereoselectivity (dr > 20:1). Demonstrating its synthetic utility, this protocol enables a five-step linear synthesis of lactone 13-a key precursor for anti-HIV and anticancer nucleoside analogues-from homoallylic alcohol 5af in a remarkable 85% overall yield.
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