The Enantioselective Synthesis of Chiral Carbocyclic Nucleosides via Palladium‐Catalyzed Asymmetric Allylic Amination of Alicyclic MBH Adducts with Purines | Zendy

Kang Bo | Zendy; Zhang QiYing | Zendy; Qu GuiRong | Zendy; Guo HaiMing | Zendy

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The Enantioselective Synthesis of Chiral Carbocyclic Nucleosides via Palladium‐Catalyzed Asymmetric Allylic Amination of Alicyclic MBH Adducts with Purines

Author(s) -

Kang Bo,

Zhang QiYing,

Qu GuiRong,

Guo HaiMing

Publication year - 2020

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.202000088

Subject(s) - chemistry , enantioselective synthesis , amination , allylic rearrangement , palladium , alicyclic compound , moiety , adduct , stereochemistry , catalysis , nucleoside , organic chemistry , combinatorial chemistry

The enantioselective synthesis of carbocyclic nucleosides through the palladium‐catalyzed asymmetric allylic amination of alicyclic Morita‐Baylis‐Hillman (MBH) adducts with purines was successfully developed. With a combination of Pd 2 (dba) 3 / L7 as catalyst, various optically active carbocyclic nucleosides featuring a C=C double bond in the carbocycle moiety were obtained in high yields (up to 97%) with excellent N 9 /N 7 ‐selectivities (>95/5) and enantioselectivities (up to >99.6%). In addition, these nucleoside analogs allowed for rapid transformation to a variety of other interesting structurally diverse chiral carbocyclic nucleosides.

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