A new type of catalytic tandem 1,4-addition-aldol reaction which proceeds through an (oxa-pi-allyl)rhodium intermediate |
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Authors: | Yoshida Kazuhiro Ogasawara Masamichi Hayashi Tamio |
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Institution: | Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan. |
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Abstract: | The reaction of 9-aryl-9-borabicyclo3.3.1]nonanes (B-Ar-9BBN) with alpha,beta-unsaturated ketones and aldehydes in the presence of 3 mol % Rh(OMe)(cod)](2) in toluene at 20 degrees 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 alpha,beta-unsaturated ketone and the aldol addition of the resulting (oxa-pi-allyl)rhodium intermediate to an aldehyde. |
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