Recent Advances in the Asymmetric Doyle-Kirmse Reaction

The asymmetric Doyle-Kirmse reaction has become in-creasingly important in the construction of chiral sulfides, especially for those with quaternary carbon stereocenters. Over the few past de -cades, a series of catalytic asymmetric approaches have been devel-oped promoted by copper, rhodium, nickel, and other chiral catalysts. Apart from the frequently investigated sulfonium ylides, the enantiose-lective [2,3]-sigmatropic rearrangement of selenium ylides and iodoni-um ylides has also been discovered recently. This review summarizes re-cent advances in the asymmetric Doyle-Kirmse reaction according to the patterns of chirality induction. The synthetic methods for rear-ranged products, reaction mechanisms and applications are discussed in this review.