Dirhodium carboxylates catalyzed enantioselective coupling reactions of α-diazophosphonates, anilines, and electron-deficient aldehydes

Cong-Ying Zhou; Jing-Cui Wang; Jinhu Wei; Zhen-Jiang Xu; Zhen Guo; Kam-Hung Low; Chi-Ming Che

doi:10.1002/anie.201206551

Dirhodium carboxylates catalyzed enantioselective coupling reactions of α-diazophosphonates, anilines, and electron-deficient aldehydes

Angew Chem Int Ed Engl. 2012 Nov 5;51(45):11376-80. doi: 10.1002/anie.201206551. Epub 2012 Oct 16.

Authors

Cong-Ying Zhou¹, Jing-Cui Wang, Jinhu Wei, Zhen-Jiang Xu, Zhen Guo, Kam-Hung Low, Chi-Ming Che

Affiliation

¹ Department of Chemistry, Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, University of Hong Kong, China.

PMID: 23074015
DOI: 10.1002/anie.201206551

Abstract

Chiral dirhodium carboxylate complexes ([Rh(2)(S-PTAD)(4)] or [Rh(2)(S-PTTL)(4)]) efficiently catalyze asymmetric three-component coupling reactions of α-diazophosphonates, anilines, and electron-deficient aldehydes to give α-amino-β-hydroxyphosphonates. The high level of enantiocontrol provides evidence for the intermediacy of metal-bound ammonium ylide in the product-forming step.

Publication types

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

MeSH terms

Aldehydes / chemistry*
Aniline Compounds / chemistry*
Azo Compounds / chemistry
Carboxylic Acids / chemical synthesis*
Carboxylic Acids / chemistry
Catalysis
Molecular Structure
Organophosphonates / chemistry*
Rhodium / chemistry*
Stereoisomerism

Substances

Aldehydes
Aniline Compounds
Azo Compounds
Carboxylic Acids
Organophosphonates
Rhodium