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Catalytic Michael/Ring‐Closure Reaction of α,β‐Unsaturated Pyrazoleamides with Amidomalonates: Asymmetric Synthesis of (−)‐Paroxetine
Author(s) -
Zhang Yu,
Liao Yuting,
Liu Xiaohua,
Yao Qian,
Zhou Yuhang,
Lin Lili,
Feng Xiaoming
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603056
Subject(s) - enantioselective synthesis , closure (psychology) , ring (chemistry) , michael reaction , catalysis , tandem , chemistry , combinatorial chemistry , monomer , stereochemistry , organic chemistry , materials science , political science , law , composite material , polymer
A highly enantioselective tandem Michael/ring‐closure reaction of α,β‐unsaturated pyrazoleamides and amidomalonates has been accomplished in the presence of a chiral N , N ′‐dioxide–Yb(OTf) 3 complex (Tf: trifluoromethanesulfonyl) to give various substituted chiral glutarimides with high yields and diastereo‐ and enantioselectivities. Moreover, this methodology could be used for gram‐scale manipulation and was successfully applied to the synthesis of (−)‐paroxetine. Further nonlinear and HRMS studies revealed that the real catalytically active species was a monomeric L ‐PMe 2 –Yb 3+ complex. A plausible transition state was proposed to explain the origin of the asymmetric induction.