Rhodium-Catalyzed Desymmetrization by Hydroformylation of Cyclopentenes: Synthesis of Chiral Carbocyclic Nucleosides

被引：34

作者：

You, Cai ^{[1
,2
]}

Wei, Biao ^{[1
,2
]}

Li, Xiuxiu ^{[1
,2
]}

Yang, Yusheng ^{[1
,2
]}

Liu, Yue ^{[1
,2
]}

Lv, Hui ^{[1
,2
]}

Zhang, Xumu ^{[1
,2
]}

机构：

[1] Wuhan Univ, Minist Educ, Key Lab Biomed Polymers, Wuhan 430072, Hubei, Peoples R China

[2] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 22期

基金：

中国国家自然科学基金;

关键词：

alkenes; diastereoselectivity; enantioselectivity; hydroformylation; rhodium; HIGHLY ENANTIOSELECTIVE HYDROFORMYLATION; ASYMMETRIC HYDROFORMYLATION; PHOSPHORAMIDITE LIGANDS; AID; ALCOHOLS; POTENT;

D O I：

10.1002/anie.201601478

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Excellent enantioselectivities (up to 97% ee) and diastereoselectivities (up to >99:1 d.r.) have been achieved in the desymmetrization of cyclopentenes by catalytic hydroformylation. This novel methodology provides an efficient and concise synthetic route to chiral cyclopentane carboxaldehydes. The key intermediate, (1S,3S)-(3-hydroxymethyl) cyclopentanol, for the synthesis of carbocyclic-ddA was obtained in three steps.

引用

页码：6511 / 6514

页数：4

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