Further Development of the Tin-Catalyzed Transcarbamoylation Reaction

Synthesis DOI: 10.1055/s-0040-1708020 Studies carried out to further develop tin-catalyzed trans­carbamoylation reactions demonstrated that transcarbamoylation of cinnamyl alcohol in the context of allyl cyanate-to-isocyanate rearrangement can be efficiently carried out on a ten-gram scale and that tin-­catalyzed transcarbamoylation is a valuable alternative to the method using trichloroacetyl isocyanate. In addition, methyl carbamate was found to be an economical carabamoyl donor in tin-catalyzed transcarbamoylation, which showed broad functional group tolerance and allowed a streamlined workup procedure. Finally, a unique synthetic method was developed for the preparation of carbamate-tethered terpene glycoconjugates. [...] © Georg Thieme Verlag Stuttgart · New YorkArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synthesis - April 19, 2020 Category: Chemistry Authors: Ichikawa, Yoshiyasu Hasegawa, Tomoyuki Minami, Takahiro Sato, Hiroshi Morishita, Yukinori Ochi, Rika Masuda, Toshiya Tags: paper Source Type: research