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Rh-Catalyzed Enantioselective Diboration of Simple Alkenes: Reaction Development and Substrate Scope

Stéphane Trudeau, Jeremy B. Morgan, Mohanish Shrestha and James P. Morken*

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

S. Trudeau, J. M. Morgan, M. Shrestha, J. P. Morken, J. Org. Chem., 2005, 70, 9538-9544.

DOI: 10.1021/jo051651m (free Supporting Information)


Abstract

A rhodium-catalyzed enantioselective syn addition of bis(catecholato)diboron to simple alkenes in the presence of (S)-Quinap provides enantioenriched 1,2-diols after subsequent oxidation. The substrate scope, the reaction mechanism, and competing pathways are discussed.

see article for more examples and reactions



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

1,2-Diols, Diboration, Hydrogen Peroxide


ID: J42-Y2005-1940