Journal ArticleDOI
Formation stéréocontroˆlée de deux centres chiraux contigus par thio-rearrangement de claisen d'α-hydroxydithioacétals de cétène s-allylés.
Pieire Beslin,Stéphane Perrio +1 more
TLDR
In this article, a transition state model is proposed to explain the observed asymmetric induction by the external hydroxy group as a result of both steric and stereoelectronic control.About:
This article is published in Tetrahedron.The article was published on 1991-08-05. It has received 22 citations till now. The article focuses on the topics: Ketene & Claisen rearrangement.read more
Citations
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Journal ArticleDOI
New aspects of the Ireland and related Claisen rearrangements
Book ChapterDOI
Thiocarbonyl Compounds as Specific Tools for Organic Synthesis
TL;DR: Thiocarbonyl compounds (thioamides, thioesters, thioketones...) react readily with a large variety of reagents (nucleophiles, electrophiles and radicals) due to their weak C=S bond and the aptitude of sulfur to stabilise an adjacent charge or radical center as discussed by the authors.
Book ChapterDOI
Sulfur Participation in [3,3]-Sigmatropic Rearrangements
TL;DR: The thio-Claisen rearrangement is a general and facile process that is often advantageous over the standard Claisen rearrANGement and involves a [3,3]-sigmatropicrearrangement of a zwitterionic intermediate.
Journal ArticleDOI
The Ireland-Claisen rearrangement as a probe for the diastereoselectivity of nucleophilic attack on a double bond adjacent to a stereogenic centre carrying a silyl group.
Mark S. Betson,Ian Fleming +1 more
TL;DR: Ireland-Claisen rearrangements largely in the same stereochemical sense as their allyl counterparts, but with moderately high levels of diastereocontrol in setting up the third stereogenic centre following from chair-like transition structures.
References
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Book
Studies in natural products chemistry
TL;DR: The series covers the synthesis or testing and recording of the medicinal properties of natural products, providing cutting edge accounts of the fascinating developments in the isolation, structure elucidation, synthesis, biosynthesis and pharmacology of a diverse array of bioactive natural products.
Journal ArticleDOI
Allylic 1,3-strain as a controlling factor in stereoselective transformations
TL;DR: In this article, the authors present a model for controlling dyadic add-ion reactions to double-branched double-bond reactions, including the following: 1.3-Strain Control of Dlastereoselective Intermolecular Addhion Reactions InvoMng Heteroallyl Systems 10.5.
Journal ArticleDOI
The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation
Related Papers (5)
Stereochimie de la deprotonation et de la reaction d'aldolisation des dithioesters
Pierre Beslin,Yannick Vallee +1 more