Enantioselective Synthesis of (Thiolan-2-yl)diphenylmethanol and Its Application in Asymmetric, Catalytic Sulfur Ylide-Mediated Epoxidation

Abstract

This work describes an expeditious and efficient preparation of enantiopure (thiolan-2-yl)diphenylmethanol (2) featuring a double nucleophilic substitution and Shi epoxidation as key steps. One of the applications of its benzyl ether derivative to asymmetric sulfur ylide-mediated epoxidation with up to 92% ee (14 examples) was also demonstrated herein.

Can acyclic conformational control be achieved via a sulfur–fluorine gauche effect?

“…Structures 2 , 3 and 4 were prepared from the intermediate 1 ( Scheme 1 ). 13 Direct deoxyfluorination of 1 was facile and furnished 2 in 54% yield. This is noteworthy given the dearth of information of fluorination of this substrate class.…”

Metal‐Free Multicomponent Reaction for Synthesis of 4,5‐Disubstituted 1,2,3‐(NH)‐Triazoles

“…Notably, formalin is also efficiently converted into the corresponding product 2 t , e. g. this multi‐component reaction proceeds well in aqueous solution. More importantly, no epoxide product was observed in any of these cases …”

Asymmetric Organocatalytic Aziridination: Recent Advances

“…should represent a suitable final example . Exploiting their experience in the enantioselective preparation of trans ‐epoxides, the Asian group initially constructed the tetrahydrothiophene‐derived chiral sulphides 97 , which was subsequently employed as catalyst in the imino Corey‐Chaykovsky reaction of benzyl bromide 96 and various substituted phenylmethanimines 95 (Scheme ). The desired aziridines 98 were easily isolated in good yields (73‐93%) and interesting optical purity (up to 83 : 17 d.r., 95–98% ee ).…”