Asymmetric Construction of Acyclic 1,3‐Nonadjacent Stereogenic Centers Containing a Tetrasubstituted Carbon through Diastereoselective Alkylation of Benzyl Sulfone Derivatives

Abstract

A strategy for the asymmetric construction of acyclic 1,3‐nonadjacent stereogenic centers containing a tetrasubstituted carbon has been established, which involves an enantioselective addition reaction and a subsequent chelate‐controlled diastereoselective alkylation reaction. Specifically, the enantioselective addition reaction of α‐thioacetamides with α‐phenyl‐substituted vinyl sulfones under chiral Brønsted base catalysis and the subsequent LDA‐mediated diastereoselective methylation, allylation and benzylation at the α position of the sulfonyl group of the adducts afforded the desired enantio‐enriched products having 1,3‐nonadjacent stereogenic centers containing a tetrasubstituted carbon in a highly stereoselective manner.