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

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).