Palladium(0)-catalyzed alkylative cyclization of alkynals and alkynones: remarkable trans-addition of organoboronic reagents |
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Authors: | Tsukamoto Hirokazu Ueno Tatsuhiko Kondo Yoshinori |
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Institution: | Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Aoba-ku, Sendai 980-8578, Japan. |
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Abstract: | Palladium/monophosphine complexes catalyze trans-selective arylative, alkenylative, and alkylative cyclization reactions of alkynals and alkynones with organoboronic reagents. These reactions afford six-membered allylic alcohols with endo-tri- or tetrasubstituted olefin groups and/or five-membered counterparts with exo olefin groups. The ratios of these products are dramatically affected by alkyne substituents as well as the phosphine ligand. The remarkable trans-selectivity of the process results from the novel reaction mechanism involving oxidative addition without oxametallacycle formation. |
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