511284-07-4Relevant articles and documents
Catalytic Michael/Ring-Closure Reaction of α,β-Unsaturated Pyrazoleamides with Amidomalonates: Asymmetric Synthesis of (?)-Paroxetine
Zhang, Yu,Liao, Yuting,Liu, Xiaohua,Yao, Qian,Zhou, Yuhang,Lin, Lili,Feng, Xiaoming
supporting information, p. 15119 - 15124 (2016/10/11)
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)3complex (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-PMe2–Yb3+complex. A plausible transition state was proposed to explain the origin of the asymmetric induction.
A novel chiral base mediated glutarimide desymmetrisation: Application to the asymmetric synthesis of (-)-paroxetine
Greenhalgh, Daniel A.,Simpkins, Nigel S.
, p. 2074 - 2076 (2007/10/03)
The asymmetric desymmetrisation of certain 4-aryl substituted glutarimides has been accomplished with high levels of selectivity (up to 97% ee) by enolisation with a chiral bis-lithium amide base. The selectivity of the reaction is shown to be the result of asymmetric enolisation, followed by a kinetic resolution. One of the chiral imides synthesised was converted into the selective seratonin reuptake inhibitor (-)-paroxetine.
