Application of chiral sulfoxides in asymmetric synthesis

Over the last three decades, the sulfinyl group has received considerable attention in asymmetric synthesis1‒5 as a chiral tool. The sulfinyl group is widely used as to bring about numerous asymmetric transformations. The effectiveness of the sulfoxide in diastereoselective auxiliary-induced reactions is mainly due to the steric and stereo electronic differences existing between the substituents on the stereogenic sulfur atom: a lone electron pair, oxygen, and two different carbon ligands, which are able to differentiate the diastereotopic faces of a proximal or even remote reaction center. Besides the high configurational stability of the sulfinyl group,6,7 the existence of several efficient methods to obtain homochiral sulfoxide as well as their synthetic versatility has led to a substantial growth of the use of these chiral starting materials in the synthesis of enantiomerically enriched compounds and in the total synthesis of numerous biologically active natural products.