Synthesis of chiral cyclobutanes via rhodium/diene-catalyzed asymmetric 1,4-addition: a dramatic ligand effect on the diastereoselectivity

Ya-Jing Chen; Tian-Jiao Hu; Chen-Guo Feng; Guo-Qiang Lin

doi:10.1039/c5cc02023a

Synthesis of chiral cyclobutanes via rhodium/diene-catalyzed asymmetric 1,4-addition: a dramatic ligand effect on the diastereoselectivity

Chem Commun (Camb). 2015 May 25;51(42):8773-6. doi: 10.1039/c5cc02023a.

Authors

Ya-Jing Chen¹, Tian-Jiao Hu, Chen-Guo Feng, Guo-Qiang Lin

Affiliation

¹ CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China. fengcg@sioc.ac.cn.

PMID: 25912603
DOI: 10.1039/c5cc02023a

Abstract

A highly diastereo- and enantioselective rhodium-catalyzed arylation of cyclobutenes for the efficient synthesis of chiral cyclobutanes has been developed. Chiral diene ligands exhibited excellent capability for the reaction diastereoselectivity control.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkadienes / chemistry*
Catalysis
Crystallography, X-Ray
Cyclobutanes / chemical synthesis*
Cyclobutanes / chemistry
Ligands
Models, Molecular
Molecular Structure
Organometallic Compounds / chemistry*
Rhodium / chemistry*
Stereoisomerism

Substances

Alkadienes
Cyclobutanes
Ligands
Organometallic Compounds
Rhodium