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Palladium‐Catalyzed Asymmetric Allylic Allylation of Racemic Morita–Baylis–Hillman Adducts
Author(s) -
Wang Xubin,
Wang Xiaoming,
Han Zhaobin,
Wang Zheng,
Ding Kuiling
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201609332
Subject(s) - chemistry , palladium , allylic rearrangement , adduct , phosphine , enantioselective synthesis , catalysis , ligand (biochemistry) , stereocenter , stereochemistry , organic chemistry , medicinal chemistry , receptor , biochemistry
A palladium‐catalyzed asymmetric allyl–allyl cross‐coupling of acetates of racemic Morita–Baylis–Hillman adducts and allylB(pin) has been developed using a spiroketal‐based bis(phosphine) as the chiral ligand, thus affording a series of chiral 1,5‐dienes bearing a vinylic ester functionality in good yields, high branched regioselectivities, and uniformly excellent enantioselectivities (95–99 % ee). Further synthetic manipulations of the allylation products provided novel ways for rapid access to a range of chiral polycyclic lactones and polycyclic lactams, as well as the antidepressant drug (−)‐Paroxetine, in high optical purities.