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Molecules
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Baylis-Hillman Reaction and Related Processes
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Baylis-Hillman Reaction and Related Processes

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (31 January 2010) | Viewed by 42023

Special Issue Editor

Prof. Dr. Guigen Li

E-Mail Website
Guest Editor
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA
Interests: synthetic methodologies; new chiral reagents; asymmetric synthesis and catalysis; new chirality and aggregational control of chirality
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Published Papers (3 papers)

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Research

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12 pages, 257 KiB  
Communication
Enantiopure Derivatives of Aza-Baylis-Hillman Adducts by Subsequent SN′-SN′ Reactions of Acylcarbamates Bearing a Chiral Auxiliary
by Gianluca Martelli, Eleonora Marcucci, Mario Orena and Samuele Rinaldi
Molecules 2009, 14(8), 2824-2835; https://doi.org/10.3390/molecules14082824 - 30 Jul 2009
Cited by 3 | Viewed by 9353
Abstract
Reactions of(4S,5R)-1-(3,4-Dimethyl-2-oxo-5-phenylimidazolidine)carbonyl-isocyanate (4) with appropriate Baylis-Hillman adducts 5 gave the corresponding acyl carbamates 6,7 as equimolar diastereomeric mixtures. These mixtures were treated with DABCO, to afford with moderate diastereoselection easily separable [2-(3",4"-dimethyl-2"-oxo-5"-phenylimidazolidine-1-carboxamido)(aryl)methyl]acrylates 8 and 9. Full article
(This article belongs to the Special Issue Baylis-Hillman Reaction and Related Processes)
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Review

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26 pages, 797 KiB  
Review
Enantioselective, Organocatalytic Morita-Baylis-Hillman and Aza-Morita-Baylis-Hillman Reactions: Stereochemical Issues
by Javier Mansilla and José M. Saá
Molecules 2010, 15(2), 709-734; https://doi.org/10.3390/molecules15020709 - 1 Feb 2010
Cited by 93 | Viewed by 14568
Abstract
Conscious of the importance that stereochemical issues may have on the design of efficient organocatalyts for both Morita-Baylis-Hillman and aza-Morita-Baylis-Hillman reaction we have analyzed them in this minireview. The so-called standard reactions involve “naked” enolates which therefore should lead to the syn adducts [...] Read more.
Conscious of the importance that stereochemical issues may have on the design of efficient organocatalyts for both Morita-Baylis-Hillman and aza-Morita-Baylis-Hillman reaction we have analyzed them in this minireview. The so-called standard reactions involve “naked” enolates which therefore should lead to the syn adducts as the major products, irrespective of the E, Z stereochemistry of the enolate. Accordingly, provided the second step is rate determining step, the design of successful bifunctional or polyfunctional catalysts has to consider the geometrical requirements imposed by the transition structures of the second step of these reactions. On the other hand, MBH and aza-MBH reactions co-catalyzed by (S)-proline and a secondary or tertiary amine (co-catalyst) involve the aldol-type condensation of either a 3-amino-substituted enamine, dienamine, or both, depending on the cases. A Zimmerman-Traxler mechanism defines the stereochemical issues regarding these co-catalyzed condensations which parallel those of the well established (S)-proline catalyzed aldol-like reactions. Full article
(This article belongs to the Special Issue Baylis-Hillman Reaction and Related Processes)
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33 pages, 737 KiB  
Review
The Morita-Baylis-Hillman Reaction: Insights into Asymmetry and Reaction Mechanisms by Electrospray Ionization Mass Spectrometry
by Verónica Carrasco-Sanchez, Mario J. Simirgiotis and Leonardo S. Santos
Molecules 2009, 14(10), 3989-4021; https://doi.org/10.3390/molecules14103989 - 12 Oct 2009
Cited by 71 | Viewed by 16719
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Baylis-Hillman Reaction and Related Processes)
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