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ۼ : 18-05-10 13:28
[2018.05]̿ȣ Pd-Catalyzed Regioselective Asymmetric Addition Reaction of Unprotected Pyrimidines to Alkoxyallene
 ۾ :
ȸ : 56  

Pd-Catalyzed Regioselective Asymmetric Addition Reaction of

Unprotected Pyrimidines to Alkoxyallene

 

Soyeong Kang, Seok Hyeon Jang, Juyeol Lee, Dong-gil Kim, Mijin Kim, Wook Jeong,

and Young Ho Rhee

 

Ī ˸Ź ̿ؼ ȣⰡ N-׷ΰ ۶ڻ̵带 ռϴ Ͽ. N-۶ڻ̵ ռ üü ؼ ӽ Ȱȭ ۿ⸦ ϰų λ깰 ߻ϴ ִ. ̱ݼ ˸Ÿ ̿ؼ ü ȣⰡ Ǹ̵ پ ۿ⸦ ϰ ִ alkoxyallene ġ ÷ϰ, λ깰 ȿ Ͽ. ش õ ϴ ͻӸ ƴ϶ ʴ N-׷ΰ ۶ڻ̵ ü ռ ؼ ռ ȮϿ.

ռ ִ 5-flourouracilκ Ī ˸Ź, ȭ ȭ ؼ ׾ ǰ ִ (-)-Tegafur ռν Ͽ. ̱ȭȸ ϴ ȭ ͽ(Organic Letters) Ǿ.


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.

 
 

Total 83
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82 [2018.05]̿ȣ Palladium-Catalyzed Asymmetric Nitrogen-Selective Addition Reaction of Indoles to Alkoxyallenes 05-10 63
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80 [2018.05]̿ȣ Pd-Catalyzed Regioselective Asymmetric Addition Reaction of Unprotected Pyrimidines to Alkoxyallene 05-10 57
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