An ylide transformation of rhodium(I) carbene: enantioselective three-component reaction through trapping of rhodium(I)-associated ammonium ylides by β-nitroacrylates

Xiaochu Ma; Jun Jiang; Siying Lv; Wenfeng Yao; Yang Yang; Shunying Liu; Fei Xia; Wenhao Hu

doi:10.1002/anie.201407740

An ylide transformation of rhodium(I) carbene: enantioselective three-component reaction through trapping of rhodium(I)-associated ammonium ylides by β-nitroacrylates

Angew Chem Int Ed Engl. 2014 Nov 24;53(48):13136-9. doi: 10.1002/anie.201407740. Epub 2014 Oct 5.

Authors

Xiaochu Ma¹, Jun Jiang, Siying Lv, Wenfeng Yao, Yang Yang, Shunying Liu, Fei Xia, Wenhao Hu

Affiliation

¹ Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Department of Chemistry, East China Normal University, Shanghai, 200062 (China).

PMID: 25284605
DOI: 10.1002/anie.201407740

Abstract

The chiral Rh(I)-diene-catalyzed asymmetric three-component reaction of aryldiazoacetates, aromatic amines, and β-nitroacrylates was achieved to obtain γ-nitro-α-amino-succinates in good yields and with high diastereo- and enantioselectivity. This reaction is proposed to proceed through the enantioselective trapping of Rh(I)-associated ammonium ylides by nitroacrylates. This new transformation represents the first example of Rh(I)-carbene-induced ylide transformation.

Keywords: ammonium ylide; carbenes; multicomponent reactions; rhodium; β-nitroacrylates.

Publication types

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

MeSH terms

Acrylates / chemistry*
Ammonium Compounds / chemistry*
Catalysis
Methane / analogs & derivatives*
Methane / chemistry
Molecular Structure
Rhodium / chemistry*
Stereoisomerism

Substances

Acrylates
Ammonium Compounds
carbene
Rhodium
Methane