手性铑膦配合物催化 α-嘌呤核苷取代丙烯酸酯的不对称氢化反应：制备替诺福韦类似物。

Asymmetric Hydrogenation of α-Purine Nucleobase-Substituted Acrylates with Rhodium Diphosphine Complexes: Access to Tenofovir Analogues.

机构信息

Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University , Xinxiang, Henan 453007, China.

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190, China.

出版信息

Org Lett. 2016 May 6;18(9):2260-3. doi: 10.1021/acs.orglett.6b00869. Epub 2016 Apr 26.

DOI:10.1021/acs.orglett.6b00869

PMID:27112983

Abstract

The first asymmetric hydrogenation of α-purine nucleobase-substituted α,β-unsaturated esters, catalyzed by a chiral rhodium (R)-Synphos catalyst, has been developed. A wide range of mono- and disubstituted acrylates were successfully hydrogenated under very mild conditions in high yields with good to excellent enantioselectivities (up to 99% ee). This method provides a convenient approach to the synthesis of a new kind of optically pure acyclic nucleoside and Tenofovir analogues.

摘要

手性铑（R）-Synphos 催化剂催化的α-嘌呤核苷取代的α,β-不饱和酯的首次不对称氢化反应已经开发出来。在非常温和的条件下，该方法可以成功地氢化各种单取代和二取代的丙烯酸酯，以高收率和优异的对映选择性（高达 99%ee）得到良好到优秀的结果。该方法为合成新型光学纯无环核苷和替诺福韦类似物提供了一种便捷的途径。