期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 4, 页码 1116-1119出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201609332
关键词
allylic compounds; asymmetric catalysis; heterocycles; palladium; P ligands
资金
- Ministry of Science of Technology of China [2016YFA0202900]
- NSFC [21232009, 20421091]
- CAS [QYZDY-SSW-SLH012]
- Science and Technology Commission of Shanghai Municipality
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.
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