Synthesis of diarylmethyl thioethersviaa DABCO-catalyzed 1,6-conjugate addition reaction ofp-quinone methides with organosulfur reagents

Abstract

A rapid and simple method was developed for the synthesis of diarylmethyl thioethers via a DABCO-catalyzed 1,6-conjugate addition reaction of para-quinone methides (p-QMs) with organosulfur reagents.

Base-catalyzed diastereodivergent thia-Michael addition to chiral β-trifluoromethyl-α,β-unsaturated N-acylated oxazolidin-2-ones

“…On the other hand, in the presence of a catalytic amount of DABCO (conditions B, Tables 2 and 3), the addition of DABCO to 1B is proposed to take place first according to the ability of DABCO to undergo 1,4-addition to an activated Michael acceptor. 21,22 Thus, the addition of DABCO from the less hindered face of 1B gives the corresponding zwitterion F , which consecutively abstracts a proton from the reaction media to form G . Finally, the S N 2 substitution of thiol at the N -containing chiral center of G gives ( R , R )- 3B as a major product and releases DABCO back to the catalytic cycle [Scheme 1(b)].…”