Chiral sulfoxides are highly important structural motifs that find wide application in asymmetric synthesis and the pharmaceutical industry. While traditional access to chiral sulfoxides mainly relies on asymmetric oxidation of the sulfide center, innovation in catalytic strategy can lead to new and valuable analogs. Herein, we present an unprecedented enantioselective imine condensation approach, resulting in efficient kinetic resolution of sulfoxide molecules bearing an aldehyde functionality with selectivity factor up to >100. Using this chiral acid-catalyzed process with an operationally simple procedure, chiral sulfoxides could be accessed in good yields and excellent enantioselectivities. The resultant chiral sulfoxides could be further transformed via a one-step derivatization to previously inaccessible bifunctional molecules with great potential in asymmetric synthesis.
Ng et al. (Wed,) studied this question.