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Pure Appl. Chem. 76(3), 465-475, 2004

Pure and Applied Chemistry

Vol. 76, Issue 3

Rhodium-catalyzed asymmetric addition of aryl- and alkenylboron reagents to electron-deficient olefins

T. Hayashi

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan

Abstract: Asymmetric 1,4-arylation and -alkenylation was achieved by use of organoboronic acids or their derivatives in the presence of a rhodium catalyst coordinated with binap or its related ligands. The scope of this asymmetric addition is very broad, a, b-unsaturated ketones, esters, amides, 1-alkenylphosphonates, and 1-nitroalkenes being efficiently converted into the corresponding 1,4-addition products with over 95% enantioselectivity. The catalytic cycle in water is proposed to involve three intermediates [aryl-or alkenyl-rhodium (oxa-p-allyl) rhodium, and hydroxo-rhodium] by NMR studies on the rhodium intermediates.

*Plenary and invited lectures presented at the 12th International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-12), Toronto, Ontario, Canada, 6-10 July 2003. Other lectures are published in this issue, pp. 453-695.


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