3 years ago

Pd-Catalyzed Regioselective Asymmetric Addition Reaction of Unprotected Pyrimidines to Alkoxyallene

Pd-Catalyzed Regioselective Asymmetric Addition Reaction of Unprotected Pyrimidines to Alkoxyallene
Soyeong Kang, Young Ho Rhee, Seok Hyeon Jang, Mijin Kim, Wook Jeong, Dong-gil Kim, Juyeol Lee
Catalytic 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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02332

DOI: 10.1021/acs.orglett.7b02332

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