Gold-Catalyzed Tandem Cycloisomerization-Halogenation of Chiral Homopropargyl Sulfonamides

Chao Shu; Long Li; Cang-Hai Shen; Peng-Peng Ruan; Chao-Yue Liu; Long-Wu Ye

doi:10.1002/chem.201503891

Gold-Catalyzed Tandem Cycloisomerization-Halogenation of Chiral Homopropargyl Sulfonamides

Chemistry. 2016 Feb 12;22(7):2282-90. doi: 10.1002/chem.201503891. Epub 2016 Jan 8.

Authors

Chao Shu¹, Long Li¹, Cang-Hai Shen¹, Peng-Peng Ruan¹, Chao-Yue Liu¹, Long-Wu Ye^{2

3}

Affiliations

¹ State Key Laboratory of Physical Chemistry of Solid Surfaces and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, Fujian, P. R. China.
² State Key Laboratory of Physical Chemistry of Solid Surfaces and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, Fujian, P. R. China. longwuye@xmu.edu.cn.
³ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, P. R. China. longwuye@xmu.edu.cn.

PMID: 26749432
DOI: 10.1002/chem.201503891

Abstract

Two new gold-catalyzed tandem cycloisomerization-halogenation reactions of chiral homopropargyl sulfonamides have been developed. Various enantioenriched 3,3-diiodopyrrolidin-2-ols and 3-fluoropyrrolidin-2-ols were obtained in moderate-to-good yields with excellent enantio- and diastereoselectivity.

Keywords: cycloisomerization; gold; halogenation; heterocycles; homogeneous catalysis.

Publication types

Research Support, Non-U.S. Gov't