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 inOrganic letters Vol. 19; no. 24; pp. 6494 - 6497
Main Authors Li, Jian-Ping, Zhao, Guo-Feng, Wang, Hai-Xia, Xie, Ming-Sheng, Qu, Gui-Rong, Guo, Hai-Ming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.12.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
METHYLENECYCLOPROPANE ANALOGS
PURINE NUCLEOSIDES
ENTECAVIR
CYCLOADDITION
INITIATED RING-CLOSURE
CHRONIC HEPATITIS-B
CARBOCYCLIC NUCLEOSIDES
NUCLEOBASE SUBSTITUTED ACRYLATES
QUATERNARY STEREOCENTERS
CYTOMEGALOVIRUS
Online AccessGet full text

Cover

More Information
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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b03110