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Enantiomerically Enriched Tris(boronates): Readily Accessible Conjunctive Reagents for Asymmetric Synthesis

John R. Coombs, Liang Zhang and James P. Morken*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States, Email: morkenbc.edu

J. R. Coombs, L. Zhang, J. P. Morken, J. Am. Chem. Soc., 2014, 136, 16140-16143.

DOI: 10.1021/ja510081r (free Supporting Information)


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Abstract

A catalytic enantioselective diboration of vinyl boronate esters furnishes chiral tris(boronates). Subsequent intermolecular or intramolecular deborylative alkylation occurs in a diastereoselective fashion.

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Pt-Catalyzed Enantioselective Diboration of Terminal Alkenes with B2(pin)2

L. T. Kliman, S. N. Mlynarski, J. P. Morken, J. Am. Chem. Soc., 2009, 131, 13210-13211.


Key Words

alkyl boronates, alkylation, dihydroxylation


ID: J48-Y2014