Stereoselective synthesis of mexiletine and structural analogs with chiral tert-butanesulfinamide. Issue 28 (8th July 2015)

• Record Type: Journal Article
• Authors: Ryan, Daniel A.; Okolotowicz, Karl J.; Mercola, Mark; Cashman, John R.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 28(2015)
• Page Start: 4195
• Page End: 4199
• Publication Date: 2015-07-08
• Subjects: Mexiletine enantiomers -- Chiral tert-butanesulfinamide -- Stereoselective reduction -- N-tert-Butanesulfinyl imines -- N-tert-Butanesulfinyl amine; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.05.041
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: An asymmetric synthesis of mexiletine and structural analogs was developed using chiral tert -butanesulfinamide to convert precursor ketones to chiral amines. Starting from α-aryloxy ketones, a two-step condensation–reduction procedure provided chiral N - tert -butanesulfinyl amines as immediate precursors to mexiletine or structural analogs. Reduction of the intermediate N - tert -butanesulfinyl imine showed substrate- and reagent-derived stereoselectivity. Following removal of the chiral auxiliary, mexiletine and structural analogs were obtained in high enantiopurity using this approach.