by Guangqing Xu, Wenzhen Fu, Guodu Liu, Chris H.
Senanayake and Wenjun Tang*
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.
Journal of the American Chemical Society
Publication Date (Web): October 22, 2013
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