Journal ArticleDOI
The intramolecular SN′ reaction
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This article is published in Tetrahedron.The article was published on 1992-09-04. It has received 64 citations till now. The article focuses on the topics: Intramolecular reaction & Nucleophilic substitution.read more
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Journal ArticleDOI
Multicomponent Linchpin Couplings. Reaction of Dithiane Anions with Terminal Epoxides, Epichlorohydrin, and Vinyl Epoxides: Efficient, Rapid, and Stereocontrolled Assembly of Advanced Fragments for Complex Molecule Synthesis
Amos B. Smith,Suresh M. Pitram,Armen M. Boldi,Matthew J. Gaunt,Chris Sfouggatakis,William H. Moser +5 more
TL;DR: The development, application, and advantages of a one-flask multicomponent dith Diane linchpin coupling protocol, over the more conventional stepwise addition of dithiane anions to electrophiles leading to the rapid, efficient, and stereocontrolled assembly of highly functionalized intermediates for complex molecule synthesis, are described.
Journal ArticleDOI
Gold(I)-catalyzed amination of allylic alcohols with cyclic ureas and related nucleophiles.
TL;DR: A 1:1 mixture of [P(t-Bu)(2)-o-biphenyl]AuCl and AgSbF(6) catalyzes the intermolecular amination of allylic alcohols with 1-methylimidazolidin-2-one and related nucleophiles that occurs with high gamma-regioselectivity and syn-stereoselectivities.
Journal ArticleDOI
Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines.
TL;DR: A 1:1 mixture of (1)AuCl and AgSbF(6) catalyzes the intramolecular amination of allylic alcohols with alkylamines to form substituted pyrrolidine and piperidine derivatives in 99% yield with 96% ee, consistent with the net syn addition of the amine relative to the departing hydroxyl group.
Journal ArticleDOI
The Importance of Hydrogen Bonding to Stereoselectivity and Catalyst Turnover in Gold-Catalyzed Cyclization of Monoallylic Diols
TL;DR: Intramolecular proton transfer and elimination provides an extremely efficient avenue for catalyst regeneration from the Au-C σ-bond intermediate, in contrast to other Au-catalyzed cyclization reactions where this intermediate severely restricts catalyst turnover.
Journal ArticleDOI
Gold(I)-Catalyzed Enantioselective Intramolecular Dehydrative Amination of Allylic Alcohols with Carbamates
TL;DR: A gold-catalyzed protocol for the intramolecular enantioselective amination of allylic alcohols with carbamates to form five- and six-membered aliphatic nitrogen heterocycles with up to 95% ee is reported.
References
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Journal ArticleDOI
Rules for ring closure
TL;DR: The endocyclic closure of nucleophilic centres to polarized double bonds to give five-membered rings is impeded by restrictions of geometry; these restrictions can be overcome in acid through the generation of oxonium or protonated forms.
Journal ArticleDOI
Stereochemistry of reaction paths at carbonyl centres
TL;DR: In this article, the reaction paths found by different methods for different nucleophiles show some striking similarities that appear to be characteristic for the reaction type, and the results of recent experimental and theoretical studies of nucleophilic addition to carbonyl groups are described.
Book ChapterDOI
Effective Molarities for Intramolecular Reactions
TL;DR: Mechanistic studies of intramolecular reactions play an important part in elucidating the chemistry of the groups involved in enzyme catalysis and in defining the mechanisms available for particular reactions.
Journal ArticleDOI
Nucleophilic and organometallic displacement reactions of allylic compounds: stereo-and regiochemistry
TL;DR: In this paper, stereo and regiochemical aspects of three reaction types: the SN2' reaction (bimolecular nucleophilic substitution with allylic rearrangement); displacement reactions effected by organometallic reagents; the conversion of allylic alcohols into halides.