Highly Enantioselective Synthesis of Chiral Cyclopropyl Nucleosides via Catalytic Asymmetric Intermolecular Cyclopropanation

An efficient route to construct chiral cyclopropyl purine nucleoside analogues has been established via the catalytic asymmetric Michael-initiated ring-closure reactions of α-purine acrylates with α-bromo-carboxylic esters. Using (DHQD)­2AQN as the catalyst, various chiral cyclopropyl purine nucleos...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2017-12, Vol.19 (24), p.6494-6497
Main Authors: Li, Jian-Ping, Zhao, Guo-Feng, Wang, Hai-Xia, Xie, Ming-Sheng, Qu, Gui-Rong, Guo, Hai-Ming
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An efficient route to construct chiral cyclopropyl purine nucleoside analogues has been established via the catalytic asymmetric Michael-initiated ring-closure reactions of α-purine acrylates with α-bromo-carboxylic esters. Using (DHQD)­2AQN as the catalyst, various chiral cyclopropyl purine nucleoside analogues with a chiral quaternary stereocenter were obtained in 72–98% yields, excellent diastereoselectivities, and 93–97% ee. Through simple functional group transformations, diverse chiral cyclopropyl purine nucleosides with hydroxymethyl group or carboxyl group were obtained.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b03110