Rhodium-Catalyzed Asymmetric 1,4-Addition of Organoboronic Acids and Their Derivatives to Electron Deficient Olefins
- 31 December 2001
- journal article
- account
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 2001 (Special ) , 0879-0887
- https://doi.org/10.1055/s-2001-14657
Abstract
Asymmetric 1,4-arylation and -alkenylation was achieved by use of organoboronic acids or their derivatives in the presence of a rhodium catalyst coordined with binap ligand. The reaction conditions are unique in that it is usually carried out in an aqueous solvent at 100 °C. The scope of this asymmetric addition is very broad, α,β-unsaturated ketones, esters, 1-alkenylphosphonates, and 1-nitroalkenes being efficiently converted into the corresponding optically active 1,4-addition products with over 95% enantioselectivity. The catalytic cycle is proposed to involve the enantioselective addition of aryl- or alkenyl-rhodium intermediate to carbon-carbon double bond of the electron deficient olefins as a key step.Keywords
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