Terminal aziridines by alpha-deprotonation/electrophile trapping of N-protected aziridine.

N-tert-Butylsulfonyl and N-tert-butylsulfinyl aziridine undergo alpha-lithiation/electrophile trapping providing a new entry to terminal aziridines. With N-tert-butylsulfinyl aziridine complete asymmetric induction is observed alpha to nitrogen.

Bibliografiske detaljer
Main Authors:	Hodgson, D, Hughes, S, Thompson, A, Heightman, T
Format:	Journal article
Sprog:	English
Udgivet:	2008

Lignende værker

Substituted aziridines by lithiation-electrophile trapping of terminal aziridines.
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Udgivet: (2005)

Lithiation: Electrophile trapping of simple aziridine building blocks
af: Hughes, S, et al.
Udgivet: (2007)

Deprotonation-electrophile trapping of terminal epoxides.
af: Hodgson, D, et al.
Udgivet: (2005)

Dimerization of lithiated terminal aziridines.
af: Hodgson, D, et al.
Udgivet: (2006)

Dimerization and isomerization reactions of alpha-lithiated terminal aziridines.
af: Hodgson, D, et al.
Udgivet: (2007)

Intramolecular cyclopropanation of unsaturated terminal aziridines.
af: Hodgson, D, et al.
Udgivet: (2006)

Efficient base catalyzed alkylation reactions with aziridine electrophiles.
af: Moss, T, et al.
Udgivet: (2008)

Aziridine electrophiles in the functionalisation of peptide chains with amine nucleophiles.
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Udgivet: (2015)

Terminal Aziridines by Addition of Grignard Reagents or Organoceriums to an (alpha-Chloro)sulfinylimine
af: Hodgson, D, et al.
Udgivet: (2009)

Asymmetric synthesis of terminal N-tert-butylsulfinyl aziridines from organoceriums and an alpha-chloroimine.
af: Hodgson, D, et al.
Udgivet: (2008)

Enantioselective synthesis of epoxides by alpha-deprotonation--electrophile trapping of achiral epoxides.
af: Hodgson, D, et al.
Udgivet: (2003)

First direct deprotonation-electrophile trapping of simple epoxides: synthesis of alpha,beta-epoxysilanes from terminal epoxides.
af: Hodgson, D, et al.
Udgivet: (2001)

Widening the usefulness of epoxides and aziridines in synthesis
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Udgivet: (2007)

Metalated Epoxides and Aziridines in Synthesis
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Udgivet: (2006)

Lithiation-induced migrations from nitrogen to carbon in terminal aziridines.
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Udgivet: (2007)

Structure and reactivity of bicyclic methylene aziridines prepared by intramolecular aziridination of allenes.
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Udgivet: (2010)

Aziridinations of tethered allenes
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Udgivet: (2011)

Preface to “Aziridine Chemistry”
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Expanding the utility of lithiated epoxides and aziridines in synthesis
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α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines.
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Coupling of 1-alkyl-2-(bromomethyl)aziridines with heteroatom-centered nucleophiles towards 2-[(heteroatom)methyl]aziridines
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Organocatalyzed enantioselective desymmetrization of aziridines and epoxides
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Udgivet: (2013-08-01)

Unexplored Nucleophilic Ring Opening of Aziridines
af: Ana María Costero, et al.
Udgivet: (2010-12-01)

α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines
af: David. M. Hodgson, et al.
Udgivet: (2010-10-01)

Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis
af: Jingran Tao, et al.
Udgivet: (2014-06-01)

Unsaturated 1,2-amino alcohols and ethers from aziridines and organolithiums.
af: Hodgson, D, et al.
Udgivet: (2004)

Enantio- and diastereoselective catalytic alkylation reactions with aziridines.
af: Moss, T, et al.
Udgivet: (2008)

Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines
af: Alan Armstrong, et al.
Udgivet: (2012-10-01)

Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines
af: Yelong Lei, et al.
Udgivet: (2022-01-01)

Pd-Catalyzed Cycloaddition of Bicyclic Aziridine with Isocyanates
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The stereodivergent aziridination of allylic carbamates, amides and sulfonamides
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Udgivet: (2023-10-01)

Asymmetric synthesis of 4H-1,3-dioxins and investigations in the metal catalyzed aziridination: aziridination versus insertion and stereoselective course
af: Susanne Flock, et al.
Udgivet: (2007-03-01)