Next Article in Journal
Design and Applications of Biodegradable Polyester Tissue Scaffolds Based on Endogenous Monomers Found in Human Metabolism
Next Article in Special Issue
Enantioselective, Organocatalytic Morita-Baylis-Hillman and Aza-Morita-Baylis-Hillman Reactions: Stereochemical Issues
Previous Article in Journal
Selenium in Oncology: From Chemistry to Clinics
Previous Article in Special Issue
Enantiopure Derivatives of Aza-Baylis-Hillman Adducts by Subsequent SN′-SN′ Reactions of Acylcarbamates Bearing a Chiral Auxiliary
Article Menu

Article Versions

Export Article

Open AccessReview
Molecules 2009, 14(10), 3989-4021;

The Morita-Baylis-Hillman Reaction: Insights into Asymmetry and Reaction Mechanisms by Electrospray Ionization Mass Spectrometry

Laboratory of Asymmetric Synthesis, Chemistry Institute of Natural Resources, Universidad de Talca, P.O. Box 747, Talca, Chile
Department of Forestry, University of Concepción, J. A. Coloma 201, Los Angeles, Chile
Author to whom correspondence should be addressed.
Received: 24 August 2009 / Revised: 1 October 2009 / Accepted: 10 October 2009 / Published: 12 October 2009
(This article belongs to the Special Issue Baylis-Hillman Reaction and Related Processes)
PDF [737 KB, uploaded 18 June 2014]   |  


This short review presents new insights on the mechanism and online monitoring using electrospray ionization tandem mass spectrometry (ESI–MS/MS) of Morita–Baylis–Hillman (MBH) reactions. MBH reactions are versatile carbon-carbon organocatalyzed bond forming reactions, making them environmentally friendly due to general organocatalysts employed. The organocatalyst behavior, which controls the transition state and thus the enantioselectivities in the obtained products, is very important in the performance of asymmetric MBH transformations. Some recent techniques and advances in asymmetric transformations are reviwed, as well as online reaction monitoring and analysis of the reaction intermediates. The mechanism accepted nowadays is also review through the insights gained from the use of ESI–MS/MS techniques.
Keywords: Morita-Baylis-Hillman; reaction mechanism; ESI-MS; online screening Morita-Baylis-Hillman; reaction mechanism; ESI-MS; online screening

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Share & Cite This Article

MDPI and ACS Style

Carrasco-Sanchez, V.; Simirgiotis, M.J.; Santos, L.S. The Morita-Baylis-Hillman Reaction: Insights into Asymmetry and Reaction Mechanisms by Electrospray Ionization Mass Spectrometry. Molecules 2009, 14, 3989-4021.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top