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Special Issue "Claisen Rearrangement"

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

Deadline for manuscript submissions: closed (31 October 2012)

Special Issue Editor

Guest Editor
Prof. Dr. Arnaud Haudrechy

Reims Molecular Chemistry Institute, Reims Champagne-Ardenne University, Moulin de la Housse, BP 1039-51687 Reims Cedex 2, France
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Interests: carbohydrate chemistry; total synthesis of natural products

Special Issue Information

Dear Colleagues,

Exactly one century ago, the discovery of the Claisen rearrangement opened the way to many approaches (of what? Towards what?) for the organic chemist. Nice extensions address stereochemical aspects, allowing prediction of the relative final arrangements, the influence of solvents, temperature and catalysts on the reaction behavior. Chirality transfers have proven to be fascinating and several examples in the field of synthesis of biologically active compounds have also been considered.

This Special Issue on Claisen Rearrangement will offer an attractive forum to present the different aspects of this marvellous reaction. I highly encourage authors to submit papers for this Special Issue, within the scope of Molecules. I hope that the topics presented will cover the enormous potential and demonstrate its widespread usefulness.

Prof. Dr. Arnaud Haudrechy
Guest Editor

Keywords

  • Claisen Rearrangement
  • Carroll Rearrangement
  • Eschenmoser Rearrangement
  • Johnson Rearrangement
  • Ireland-Claisen Rearrangement
  • Reformatsky-Claisen Rearrangement
  • Enzymatic Claisen Rearrangement

Published Papers (3 papers)

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Research

Open AccessArticle Tandem RCM–Claisen Rearrangement–[2+2] Cycloaddition of O,O'-(But-2-en-1,4-diyl)-bridged Binaphthols
Molecules 2012, 17(12), 14531-14554; doi:10.3390/molecules171214531
Received: 30 October 2012 / Revised: 29 November 2012 / Accepted: 3 December 2012 / Published: 7 December 2012
Cited by 2 | PDF Full-text (546 KB) | Supplementary Files
Abstract
Attempted RCM of 2,2'-bis(allyloxy)-1,1'-binaphthyl resulted in a Claisen-type rearrangement of a postulated labile dioxacyclodecine proceeding at room temperature and followed by [2+2] cycloaddition. Structures of products were confirmed by X-ray crystallography. A mechanistic rationalisation based on relative stabilities of proposed intermediates and transition
[...] Read more.
Attempted RCM of 2,2'-bis(allyloxy)-1,1'-binaphthyl resulted in a Claisen-type rearrangement of a postulated labile dioxacyclodecine proceeding at room temperature and followed by [2+2] cycloaddition. Structures of products were confirmed by X-ray crystallography. A mechanistic rationalisation based on relative stabilities of proposed intermediates and transition states is provided. Full article
(This article belongs to the Special Issue Claisen Rearrangement)
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Open AccessArticle Recent Developments in the Reformatsky-Claisen Rearrangement
Molecules 2012, 17(12), 14249-14259; doi:10.3390/molecules171214249
Received: 8 November 2012 / Revised: 21 November 2012 / Accepted: 27 November 2012 / Published: 30 November 2012
Cited by 4 | PDF Full-text (378 KB) | HTML Full-text | XML Full-text
Abstract
The rearrangement of allyl a-bromoacetates with Zn dust is known as the Reformatsky-Claisen rearrangement. Whereas the Ireland-Claisen rearrangement has been widely used in the synthesis of a diverse range of natural products, the Zn-mediated Reformatsky-Claisen rearrangement has not been utilized so often. In
[...] Read more.
The rearrangement of allyl a-bromoacetates with Zn dust is known as the Reformatsky-Claisen rearrangement. Whereas the Ireland-Claisen rearrangement has been widely used in the synthesis of a diverse range of natural products, the Zn-mediated Reformatsky-Claisen rearrangement has not been utilized so often. In this article, we will provide an overview of recent advances in the Reformatsky-Claisen rearrangement field, including the In-mediated Reformatsky-Claisen rearrangement we have recently developed. Full article
(This article belongs to the Special Issue Claisen Rearrangement)
Open AccessArticle Asymmetric Construction of All-Carbon Quaternary Stereocenters by Chiral-Auxiliary-Mediated Claisen Rearrangement and Total Synthesis of (+)-Bakuchiol
Molecules 2012, 17(11), 13330-13344; doi:10.3390/molecules171113330
Received: 9 October 2012 / Revised: 23 October 2012 / Accepted: 2 November 2012 / Published: 8 November 2012
Cited by 9 | PDF Full-text (417 KB)
Abstract
An asymmetric Claisen rearrangement using Oppolzer’s camphorsultam was developed. Under thermal conditions, a geraniol-derived substrate underwent the rearrangement with good stereoselectivity. The absolute configuration of the newly formed all-carbon quaternary stereocenter was confirmed by the total synthesis of (+)-bakuchiol from the rearrangement product.
[...] Read more.
An asymmetric Claisen rearrangement using Oppolzer’s camphorsultam was developed. Under thermal conditions, a geraniol-derived substrate underwent the rearrangement with good stereoselectivity. The absolute configuration of the newly formed all-carbon quaternary stereocenter was confirmed by the total synthesis of (+)-bakuchiol from the rearrangement product. Full article
(This article belongs to the Special Issue Claisen Rearrangement)
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