Cascade Cyclizations of α,β-Unsaturated Thioesters: Additional Examples

Abstract

Several additional examples of cascade cyclizations of α,β-unsaturated thioesters proceeding are reported, which proceed via two distinct mechanistic pathways: enantioselective acyl transfer promoted by amidine-based catalysts (ABCs) and a racemic chain mechanism mediated by a thiolate nucleophile. Note pubs.acs.org/joc

Recent developments in thiochromene chemistry

“…Ahlemeyer et al , in 2021, attempted the cascade cyclization of cinnamic acid thioesters ( 126 ), which proceeded via aldol cyclization cum lactonization to generate thiochromenes ( 130 ) under neat reaction conditions. 61 The asymmetric synthetic protocol envisaged by this group demonstrated good yields (up to 79%) with an ee of 96% using electron-rich amidine-based catalysts (Scheme 33).…”

Nickel-Catalyzed Carbonylative Synthesis of α,β-Unsaturated Thioesters from Vinyl Triflates and Arylsulfonyl Chlorides

“…They are a significant building block in the synthesis of complex molecules and natural products . Compared with alcohol-derived esters, they exhibit rich reactivity and have been found as key intermediates in various organic reactions, such as the Diels–Alder reaction, conjugated addition, cascade cyclization, intramolecular oxa-conjugate cyclization, decarbonylation, reduction, and so on. Therefore, the synthesis of α,β-unsaturated thioesters is of great interest in organic synthesis.…”