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

Verfasser / Beitragende:
[T. Hayashi]
Ort, Verlag, Jahr:
2004
Enthalten in:
Pure and Applied Chemistry, 76/3(2004-01-01), 465-475
Format:
Artikel (online)
ID: 378923153
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024 7 0 |a 10.1351/pac200476030465  |2 doi 
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100 1 |a Hayashi  |D T.  |u Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan 
245 1 0 |a Rhodium-catalyzed asymmetric addition of aryl- and alkenylboron reagents to electron-deficient olefins  |h [Elektronische Daten]  |c [T. Hayashi] 
520 3 |a 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, α, β-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-π-allyl) rhodium, and hydroxo-rhodium] by NMR studies on the rhodium intermediates. 
540 |a © 2013 Walter de Gruyter GmbH, Berlin/Boston 
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