Application of tert-Butylsulfinamide in Total Synthesis of Natural Products

Abstract

The formation of chiral amine intermediates with chiral tert-butanesulfinamide and their applications in asymmetric natural product synthesis in recent years are summarized. tert-Butanesulfinamide has attracted wide attention from chemists because it is stable, commercially available with reasonable price, ease to use, and usually induces high diastereoselectivity in the reactions involved. This review is divided into two sections, including the addition of nucleophiles to N-tert-butanesulfinyl imines and the addition of N-tert-butanesulfinyl metalloenamines to electrophiles.

Synthesis of Isothiazoles through N-Propargylsulfinylamide: TFA-Promoted Sulfinyl Group-Involved Intramolecular Cyclization

“…In the past two decades, a set of reagents based on the N - tert -butanesulfinyl scaffold fused to nitrogen-containing heterocycles were developed for simplifying stereocontrolled access to organic compounds . For example, tert -butanesulfinamide has been successfully applied in the total synthesis of many natural products, such as (+)-swainsonine, dioncophylline E, (−)-epiquinamide, (−)-vindorosine, and so on. These reagents usually can avoid the extraneous steps yet retain the high reactivity toward nucleophiles.…”