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Special Issue "Baylis-Hillman Reaction and Related Processes"

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

Deadline for manuscript submissions: closed (31 January 2010)

Special Issue Editor

Guest Editor
Prof. Dr. Guigen Li (Website)

Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA
Fax: +1 806 742 1289
Interests: halo aldol reaction; alkene additions; aminohalogenation; diamination; Baylis-Hillman reaction

Published Papers (3 papers)

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Research

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Open AccessCommunication Enantiopure Derivatives of Aza-Baylis-Hillman Adducts by Subsequent SN′-SN′ Reactions of Acylcarbamates Bearing a Chiral Auxiliary
Molecules 2009, 14(8), 2824-2835; doi:10.3390/molecules14082824
Received: 7 July 2009 / Revised: 22 July 2009 / Accepted: 30 July 2009 / Published: 30 July 2009
PDF Full-text (257 KB)
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

Jump to: Research

Open AccessReview Enantioselective, Organocatalytic Morita-Baylis-Hillman and Aza-Morita-Baylis-Hillman Reactions: Stereochemical Issues
Molecules 2010, 15(2), 709-734; doi:10.3390/molecules15020709
Received: 19 January 2010 / Revised: 25 January 2010 / Accepted: 29 January 2010 / Published: 1 February 2010
Cited by 59 | PDF Full-text (797 KB)
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 [...] 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)
Open AccessReview The Morita-Baylis-Hillman Reaction: Insights into Asymmetry and Reaction Mechanisms by Electrospray Ionization Mass Spectrometry
Molecules 2009, 14(10), 3989-4021; doi:10.3390/molecules14103989
Received: 24 August 2009 / Revised: 1 October 2009 / Accepted: 10 October 2009 / Published: 12 October 2009
Cited by 42 | PDF Full-text (737 KB)
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 [...] 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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