A New Type of Catalytic Tandem 1,4-Addition−Aldol Reaction Which Proceeds through an (Oxa-π-allyl)rhodium Intermediate
- 22 August 2002
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (37), 10984-10985
- https://doi.org/10.1021/ja0271025
Abstract
The reaction of 9-aryl-9-borabicyclo[3.3.1]nonanes (B-Ar-9BBN) with α,β-unsaturated ketones and aldehydes in the presence of 3 mol % [Rh(OMe)(cod)]2 in toluene at 20 °C for 2 h gave high yields of the tandem 1,4-addition−aldol reaction products with high syn selectivity. The reaction proceeds through the catalytic cycle consisting of 1,4-addition of an organorhodium species to an α,β-unsaturated ketone and the aldol addition of the resulting (oxa-π-allyl)rhodium intermediate to an aldehyde.Keywords
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