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Directed, Palladium(II)-Catalyzed Enantioselective anti-Carboboration of Alkenyl Carbonyl Compounds

preprint
submitted on 11.01.2019 and posted on 11.01.2019 by Zhen Liu, Xiaohan Li, Tian Zeng, Keary Engle
A substrate-directed enantioselective anti-carboboration reaction of alkenes has been developed, wherein a carbon based nucleophile and a boron moiety are installed across the C=C bond through a 5- or 6-membered palladacycle intermediate. The reaction is promoted by a palladium(II) catalyst and a mondentate oxzazoline ligand. A range of enantioenriched secondary alkylboronate products were obtained with moderate to high enantioselectivity that could be further upgraded by recrystallization. This work represents a new method to synthesize versatile and valuable alkylboronate building blocks. Building on an earlier mechanistic proposal by Peng, He, and Chen, a revised model is proposed to account for the stereoconvergent nature of this transformation.

Funding

NIH-5R35GM125052-02

History

Email Address of Submitting Author

keary@scripps.edu

Institution

The Scripps Research Institute

Country

USA

ORCID For Submitting Author

0000-0003-2767-6556

Declaration of Conflict of Interest

No conflict of interest to declare.

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