Recent Advances in Catalytic Asymmetric Reactions of Thiazolones, Rhodanines and Their Derivatives

Abstract

Sulfur‐containing skeletons are widely found in natural products, drugs and bioactive compounds. As a direct and efficient access to sulfur‐functionalized carbon stereocenters, the catalytic enantioselective reactions of sulfur‐containing prochiral carbon centers have attracted great attention in the past few years. The review summarizes the chemistry of thiazolones, rhodanines and their derivatives in the context of catalytic enantioselective construction of sulfur‐containing skeletons.

Enantioselective Synthesis of SpirothiazolonesviaCooperative Catalysis

“…To date, various synthetic methodologies for the construction of chiral thiazolone derivatives have been reported [4a,b] . In 2010, Ooi et al.…”

Catalyst-Controlled Diastereoselectivity Switch in the Asymmetric [3 + 2] Annulation of Isatin-Derived MBH Carbonates and 5-Alkenylthiazol-4(5H)-ones

“…4 Recently, 5-alkenylthiazol-4(5H)-ones became polar Michael acceptors for the construction of various privileged scaffolds featuring a thiazol-4-one motif, which was widely present in bioactive compounds (Scheme 1a). 5 Regarding the reactivity of 2benzylidene-1H-indene-1,3(2H)-dione 4 and 5-alkenylthiazol-4(5H)-one, the latter displays a much lower electrophilicity of its CC bond due to the conjugation with a sulfur atom. In addition, both the chemoselectivity and regioselectivity for the reaction of 5-alkenylthiazol-4(5H)-one 6,7 and zwitterionic ylide species generated from MBH carbonates 8,9 are also very challenging (Scheme 1b).…”