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Download fileOne-Pot Process That Efficiently Generates Single Stereoisomers of 1,3-Bisphosphinylpropanes Having Five Chiral Centers
journal contribution
posted on 2015-01-02, 00:00 authored by He Zhang, Yong-Ming Sun, Yalei Zhao, Zhong-Yang Zhou, Ji-Ping Wang, Nana Xin, Shao-Zhen Nie, Chang-Qiu Zhao, Li-Biao HanP,C-Stereogenic 1,3-bisphosphinylpropanes 3 that have up to five stereogenic centers could be obtained
stereoselectively in high yields by a one-step reaction of (RP)-menthylphenylphosphine oxide 1 with α,β-unsaturated aldehydes 2 catalyzed
by KOH at room temperature. A mechanism was proposed as to involve
a stereoselective intermolecular 1,3′-phosphorus migration
from the 1,2-adduct of 1 with 2 to another 2 generating a 1,4-adduct that subsequently reacts with 1 to produce 3.