title: Catalytic Michael/Ring-Closure Reaction of α,β-Unsaturated Pyrazoleamides with Amidomalonates: Asymmetric Synthesis of (-)-Paroxetine.
abstract: 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.
authors: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P.R. China), Fax: (+86) 28 8541 8249.
authors: Yu
authors: Y
authors: Zhang
authors: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P.R. China), Fax: (+86) 28 8541 8249.
authors: Yuting
authors: Y
authors: Liao
authors: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P.R. China), Fax: (+86) 28 8541 8249. liuxh@scu.edu.cn.
authors: Xiaohua
authors: X
authors: Liu
authors: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P.R. China), Fax: (+86) 28 8541 8249.
authors: Qian
authors: Q
authors: Yao
authors: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P.R. China), Fax: (+86) 28 8541 8249.
authors: Yuhang
authors: Y
authors: Zhou
authors: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P.R. China), Fax: (+86) 28 8541 8249.
authors: Lili
authors: L
authors: Lin
authors: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P.R. China), Fax: (+86) 28 8541 8249. xmfeng@scu.edu.cn.
authors: Xiaoming
authors: X
authors: Feng
mesh_terms: D002384:Catalysis; D017374:Paroxetine / Q000138:chemical synthesis* / Q000737:chemistry; D011720:Pyrazoles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D011720:Pyrazoles; D017374:Paroxetine
keywords: Michael reactions; asymmetric synthesis; heterocycles; paroxetine; ring-closure reactions