Synthetic Approach toward Enantiopure Cyclic Sulfinamides

Glebs Jersovs; Matiss Bojars; Pavel A Donets; Edgars Suna

doi:10.1021/acs.orglett.2c01738

Synthetic Approach toward Enantiopure Cyclic Sulfinamides

Org Lett. 2022 Jul 1;24(25):4625-4629. doi: 10.1021/acs.orglett.2c01738. Epub 2022 Jun 16.

Authors

Glebs Jersovs^{1

2}, Matiss Bojars^{1

2}, Pavel A Donets¹, Edgars Suna^{1

2}

Affiliations

¹ Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga LV-1006, Latvia.
² Department of Chemistry, University of Latvia, Jelgavas 1, Riga LV-1004, Latvia.

Abstract

A synthetic approach toward densely substituted enantiopure cyclic sulfinamides possessing up to four consecutive stereogenic centers was developed based on a completely diastereoselective S_N2' cyclization/tert-Bu cleavage sequence. Diastereospecific transformation of the obtained scaffold into chiral S^VI derivatives such as sulfoximines and sulfonimidamides is demonstrated.