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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:

J. Yuan, P. Jain, J. C. Antilla, J. Org. Chem., 2020, 85, 12988-13003.

DOI: 10.1021/acs.joc.0c01646

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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