ol7b02332_si_001.pdf (6.84 MB)
Pd-Catalyzed Regioselective Asymmetric Addition Reaction of Unprotected Pyrimidines to Alkoxyallene
journal contribution
posted on 2017-08-16, 12:48 authored by Soyeong Kang, Seok Hyeon Jang, Juyeol Lee, Dong-gil Kim, Mijin Kim, Wook Jeong, Young Ho RheeCatalytic asymmetric
synthesis of N-heterocyclic
glycosides free of protecting and directing groups is reported. The
key reaction is highlighted by the atom-efficient and regioselective
addition of unprotected pyrimidines to highly functionalized alkoxyallene.
Numerous acyclic and cyclic N-heterocyclic glycosides
are accessed with minimal formation of organic byproducts. The synthetic
utility of the reaction is demonstrated by the first catalytic asymmetric
synthesis of anticancer pharmaceutical (−)-Tegafur and stereoselective
synthesis of an oxepane nucleoside derivative.