Organocatalysts wrapped around by poly(ethylene glycol)s (PEGs): a unique host-guest system for asymmetric Michael addition reactions

Dan Qian Xu; Shu Ping Luo; Yi Feng Wang; Ai Bao Xia; Hua Dong Yue; Li Ping Wang; Zhen Yuan Xu

doi:10.1039/b708525g

Organocatalysts wrapped around by poly(ethylene glycol)s (PEGs): a unique host-guest system for asymmetric Michael addition reactions

Chem Commun (Camb). 2007 Nov 14:(42):4393-5. doi: 10.1039/b708525g. Epub 2007 Aug 17.

Authors

Dan Qian Xu¹, Shu Ping Luo, Yi Feng Wang, Ai Bao Xia, Hua Dong Yue, Li Ping Wang, Zhen Yuan Xu

Affiliation

¹ State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou, China.

PMID: 17957297
DOI: 10.1039/b708525g

Abstract

Asymmetric Michael addition reactions of unmodified ketones to nitroalkenes were performed in PEGs catalyzed by novel pyrrolidinyl-thioimidazolium salts to give products in up to 97% yield and 99% enantioselectivity; ESI mass spectrometric detection for the first time gave evidence of the presence of the PEG-organocatalyst host-guest complex.

Publication types

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

MeSH terms

Alkenes / chemical synthesis*
Catalysis
Indicators and Reagents
Ketones / chemical synthesis*
Magnetic Resonance Spectroscopy
Polyethylene Glycols / chemistry*
Pyrrolidines
Spectrometry, Mass, Electrospray Ionization
Spectrophotometry, Infrared
Stereoisomerism
X-Ray Diffraction

Substances

Alkenes
Indicators and Reagents
Ketones
Pyrrolidines
Polyethylene Glycols