Pd-Catalyzed Regioselective Asymmetric Addition Reaction of Unprotected Pyrimidines to Alkoxyallene
- Pd-Catalyzed Regioselective Asymmetric Addition Reaction of Unprotected Pyrimidines to Alkoxyallene
- Kang, Soyeong; Jang, Seok Hyeon; Lee, Juyeol; Kim, Dong-gil; Kim, Mijin; Jeong, Wook; Rhee, Young Ho
- Date Issued
- AMER CHEMICAL SOC
- 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.
- 5-SUBSTITUTED URACILS; NUCLEOSIDE ANALOGS; ALLYLIC AMINATION; TERMINAL ALLENES; METATHESIS; GLYCOSYLATION; RING; HETEROCYCLES; STRATEGY; AMINES
- Article Type
- ORGANIC LETTERS, vol. 19, no. 17, page. 4684 - 4687, 2017-09
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