Quinine-catalyzed asymmetric domino Mannich-cyclization reactions of 3-isothiocyanato oxindoles with imines for the synthesis of spirocyclic oxindoles》.pdf

Tetrahedron 71 (2015) 949e955 Contents lists available at ScienceDirect Tetrahedron journal homepage: www.elsevier.c om/locate/tet Quinine-catalyzed asymmetric domino Mannich-cyclization reactions of 3-isothiocyanato oxindoles with imines for the synthesis of spirocyclic oxindoles Mei Bai a, b, c, Bao-Dong Cui a, b, Jian Zuo a, c, Jian-Qiang Zhao a, c, Yong You a, c, Yong-Zheng Chen b, Xiao-Ying Xu a, Xiao-Mei Zhang a, Wei-Cheng Yuan a, * a National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China b School of Pharmacy, Zunyi Medical University, Zunyi 563000, China c University of Chinese Academy of Sciences, Beijing 100049, China a r t i c l e i n f o a b s t r a c t Article history: 0 A range of structurally diverse chiral spiro[imidazolidine-2-thione-4,3 -oxindole] compounds could be Received 27 October 2014 obtained via a domino Mannich-cyclization reaction of 3-isothiocyanato oxindoles and imines with Received in revised form 11 December 2014 commercial quinine as catalyst under mild conditions. The protocol is significantly characterized by Accepted 21 December 2014 simple process, easily available catalyst, high reactivity, low catalyst loading (1 mol %), and good to ex- Available online 26 December 2014 cellent diastereo-