(Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers

Beilstein J Org Chem. 2016 Mar 10:12:462-95. doi: 10.3762/bjoc.12.48. eCollection 2016.

Abstract

Organocatalysis, now running its second decade of life, is being considered one of the main tools a synthetic chemist has to perform asymmetric catalysis. In this review the synthesis of six-membered rings, that contain multiple chiral centers, either by a ring closing process or by a functionalization reaction on an already existing six-membered ring, utilizing bifunctional (thio)ureas will be summarized. Initially, the use of primary amine-thioureas as organocatalysts for the above transformation is being discussed, followed by the examples employing secondary amine-thioureas. Finally, the use of tertiary amine-thioureas and miscellaneous examples are presented.

Keywords: multiple chiral centers; organocatalysis; six-membered ring; thiourea; urea.

Publication types

  • Review