Journal ArticleDOI
Selective ring-opening reaction of styrene oxide with lithium azide in the presence of cyclodextrins in aqueous media
TLDR
In this paper, a ring-opening of racemic styrene oxide was achieved by lithium azide in the presence of β-cyclodextrin in aqueous media.Abstract:
Regioselective ring-opening of racemic styrene oxide was achieved by lithium azide in the presence of β-cyclodextrin in aqueous media. Kinetic resolution of racemic epoxide was observed and 1-phenyl-2-azido-ethanol was obtained with 78 % ee.read more
Citations
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Journal ArticleDOI
Highly Enantioselective and Regioselective Biocatalytic Azidolysis of Aromatic Epoxides
Jeffrey H. Lutje Spelberg,Johan E. T. van Hylckama Vlieg,Lixia Tang,Dick B. Janssen,Richard M. Kellogg +4 more
TL;DR: In a large scale conversion, the decrease in yield and selectivity due to the uncatalyzed chemical side reaction could be overcome by slow addition of azide.
Journal ArticleDOI
Ring-Opening of Epoxides in Water
TL;DR: In this paper, the authors highlight the unique role of water in the ring-opening reactions of epoxides and highlight the importance of water as a reaction medium for realizing processes that cannot be performed alternatively in other reaction media.
Journal ArticleDOI
Ring Opening of Epoxides with Sodium Azide in Water. A Regioselective pH-Controlled Reaction
Journal ArticleDOI
Bioformation of optically pure epoxides
TL;DR: In this paper, an overview is presented on the various biological methods available and some strong and weak points of these systems are considered, as well as a review of some of the properties of these methods.
Journal ArticleDOI
Synthesis of Optically Pure 2-Azido-1-arylethanols with Isolated Enzymes and Conversion to Triazole-Containing β-Blocker Analogues Employing Click Chemistry
TL;DR: ( S)-2-Azido-1-( p-chlorophenyl)ethanols reacted with alkynes employing click chemistry to afford high yields of optically pure triazole-containing beta-adrenergic receptor blocker analogues with potential biological activity.
References
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Journal ArticleDOI
Selective syntheses using cyclodextrins as catalyst. 2. The para-oriented carboxylation of phenols
Makoto Komiyama,Hidefumi Hirai +1 more
Journal ArticleDOI
Selective aromatic substitution by hydrophobic binding of a substrate to a simple cyclodextrin catalyst
Ronald Breslow,Peter Campbell +1 more
TL;DR: Findings strongly support a mechanism in which the cyclodextrin reacts with HOCl to form a hypochlorite, and delivers this chlorine selectively to anisole bound in its cavity.
Journal ArticleDOI
Asymmetric reduction of ketones with crystalline cyclodextrin complexes of amine-boranes
Journal ArticleDOI
Lipase-catalyzed resolution of acyclic amino alcohol precursors
Journal ArticleDOI
Cyclodextrin-H O: A New System for Asymmetric Epoxidation
TL;DR: Asymmetric epoxidation of trans-cinnam-aldehyde and chalcone by the use of H2sp>O2SP> as an oxidizing agent in alkaline media in the presence of cyclodextrins gave the corresponding epoxides with enantiomeric excess up to 8 %.
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