A new type of chiral sulfinamide monophosphine ligands: stereodivergent synthesis and application in enantioselective gold(I)-catalyzed cycloaddition reactions

Zhan-Ming Zhang; Peng Chen; Wenbo Li; Yanfei Niu; Xiao-Li Zhao; Junliang Zhang

doi:10.1002/anie.201401067

A new type of chiral sulfinamide monophosphine ligands: stereodivergent synthesis and application in enantioselective gold(I)-catalyzed cycloaddition reactions

Angew Chem Int Ed Engl. 2014 Apr 22;53(17):4350-4. doi: 10.1002/anie.201401067. Epub 2014 Mar 20.

Authors

Zhan-Ming Zhang¹, Peng Chen, Wenbo Li, Yanfei Niu, Xiao-Li Zhao, Junliang Zhang

Affiliation

¹ Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China) http://faculty.ecnu.edu.cn/s/1811/t/20975/main.jspy.

PMID: 24652597
DOI: 10.1002/anie.201401067

Abstract

A simple, new type of chiral sulfinamide monophosphines, the so-called Ming-Phos ligands, is reported; these ligands could be easily prepared from inexpensive and commercially available starting materials. The Ming-Phos ligands performed well in the enantioselective gold-catalyzed cycloaddition reaction of 2-(1-alkynyl)-alk-2-en-1-ones with nitrones. Both enantiomers of the products could be obtained in good yields and with excellent diastereo- and enantioselectivity through transformations that were catalyzed by gold complexes derived from two diastereomers of Ming-Phos ligand M5 (Ar=1-naphthyl).

Keywords: asymmetric catalysis; cycloaddition; enantioselectivity; gold; phosphine ligands.