Bi(cyclopentyl)diol-Derived Boronates in Highly Enantioselective Chiral Phosphoric Acid-Catalyzed Allylation, Propargylation, and Crotylation of Aldehydes
Jinping Yuan, Pankaj Jain and Jon C. Antilla*
*Institute for Molecular Design and Synthesis, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China,
Email: jantilla
tju.edu.cn
J. Yuan, P. Jain, J. C. Antilla, J. Org. Chem., 2020, 85, 12988-13003.
DOI: 10.1021/acs.joc.0c01646
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Abstract
Chiral phosphoric acids catalyze an enantioselective addition of bi(cyclopentyl)diol-derived boronates to aldehydes to provide homoallylic, propargylic, and crotylic alcohols with high enantiomeric excess and diastereomeric ratios. A wide substrate scope was exhibited, and the novel boronates provided high enantiocontrol.
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proposed mechanism
Key Words
homoallylic alcohols, organocatalysis
ID: J42-Y2020
