Asymmetric organocatalytic three-component 1,3-dipolar cycloaddition: control of stereochemistry via a chiral Brønsted acid activated dipole

Xiao-Hua Chen; Wen-Quan Zhang; Liu-Zhu Gong

doi:10.1021/ja801034e

Asymmetric organocatalytic three-component 1,3-dipolar cycloaddition: control of stereochemistry via a chiral Brønsted acid activated dipole

J Am Chem Soc. 2008 Apr 30;130(17):5652-3. doi: 10.1021/ja801034e. Epub 2008 Apr 3.

Authors

Xiao-Hua Chen¹, Wen-Quan Zhang, Liu-Zhu Gong

Affiliation

¹ Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.

PMID: 18386896
DOI: 10.1021/ja801034e

Abstract

A Brønsted acid catalyzed three-component asymmetric 1,3-dipolar addition reaction between aldehydes, amino esters, and dipolarophiles by a new bisphosphoric acid, derived from the linked BINOL, furnished multiply substituted pyrrolidines in high yield with excellent enantioselectivities under mild conditions.

Publication types

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

MeSH terms

Aldehydes / chemistry*
Amino Acids / chemistry*
Catalysis
Cyclization
Esters / chemistry*
Models, Chemical
Phosphoric Acids / chemistry*
Pyrrolidines / chemical synthesis*
Stereoisomerism

Substances

Aldehydes
Amino Acids
Esters
Phosphoric Acids
Pyrrolidines