Applications of tert‐Butanesulfinamide in the Asymmetric Synthesis of Amines

Abstract

tert-Butanesulfinamide is prepared using catalytic enantioselective methods in two steps from the extremely inexpensive oil waste by-product, tert-butyl disulfide. Direct condensation of tert-butanesulfinamide with aldehydes and ketones provides tert-butanesulfinyl imines in uniformly high yields. The tert-butanesulfinyl group activates the imines for the addition of many different classes of nucleophiles, serves as a powerful chiral directing group, and after nucleophilic addition is readily cleaved by treatment with acid. A wide range of highly enantioenriched amines, including α-branched and α,α-dibranched amines, α-and β-amino acids, 1,2-and 1,3-amino alcohols and α-trifluoromethyl amines are efficiently synthesized using this methodology.

Development of Orally Bioavailable and CNS Penetrant Biphenylaminocyclopropane Carboxamide Bradykinin B1 Receptor Antagonists

“…For compounds bearing a chiral center via the addition of a methyl group at the benzylic position, requisite sulfinamide 9 could be prepared from aldehyde 8 using Ellman's t-butylsulfinimine methodology. 20 Protecting group manipulation was followed by conversion of bromide 9 to pinacolboronate 10. Subsequent Suzuki coupling with the appropriate halide 14 was followed by deprotection to produce chiral biphenylamines 11a-g.…”

Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds

“… 15 Ellman and co-workers published two review papers in which tert -butanesulfinamide was presented as a useful synthetic intermediate in asymmetric reactions. 199 , 200 N -Sulfinylimines, the family of compounds of great synthetic importance, were the subject of the second part of article by Davis, who briefly described the synthesis of enantiomerically pure compounds from his group, more widely showing their great potential as chiral auxiliaries and reactants. 37 In their papers published in 2002 and 2009, respectively, Ellman’s group and Ferreira and co-workers narrowed their topic to tert -butanesulfinimines: their enantioselective preparation, postsynthetic modification, and use in asymmetric transformations, mainly in the synthesis of chiral amines.…”

Advances in Asymmetric N Construction of Metal and Organic Small Molecules

“…A wide range of highly enantioenriched amines are efficiently synthesized using this methodology. In the process of hydrogenation deoxidation imine, different chirality deoxidation products can be obtained by selecting different hydrogenation reagents [4][5][6] . ISSN 2616-5880 Vol.…”