Efficient syntheses of korupensamines A, B and michellamine B by asymmetric Suzuki-Miyaura coupling reactions.
writer：Guangqing Xu, Wenzhen Fu, Guodu Liu, Chris H Senanayake, Wenjun Tang.*
keywords：asymmetric Suzuki-Miyaura coupling reaction
source：期刊
specific source：J. Am. Chem. Soc. 2014, 136, 570–573. (DOI: 10.1021/ja409669r, IF = 14.695, Citation:162)
Issue time：2013年
Efficient asymmetric Suzuki-Miyaura coupling reactions are employed for the first time in total syntheses of chiral biaryl natural products korupensamine A and B in combination with an effective diastereoselective hydrogenation, allowing ultimately a concise and stereoselective synthesis of michellamine B. Chiral monophosphorus ligands L1–3 are effective for the syntheses of a series of functionalized chiral biaryls by asymmetric Suzuki-Miyaura coupling reactions in excellent yields and enantioselectivities (up to 99% ee). The presence of a polar-π interaction between the highly polarized BOP group and the extended π system of arylboronic acid coupling partner is believed to be important for the high enantioselectivity.