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- W2003147006 abstract "The chemistry and synthetic utility of α-lithiated haloalkyloxazolines, oxazolinyl epoxides, and aziridines are highlighted in this account. These lithiated species, which are easily generated, can be captured by electrophiles to give more functionalized derivatives. Spectroscopic and computational studies have proved useful, not only in relation to understanding the chemistry of lithiated species in general, but also in the elucidation of the mechanisms of their lithiation and the stereochemistry of their reactions. The combination of bench experiments with spectroscopic investigations and density functional theory calculations has contributed enormously to increasing the synthetic potential of the lithiated oxazolines that are described in this account. 1Introduction 2Lithiation and Reactions of 2-(Haloalkyl)oxazolines and Their Applications 2.1Synthesis of Oxazolinyl and Formyl Epoxides 2.2Synthesis of Oxazolinylcyclopropanes 2.3Synthesis of Oxazolinyl Estrones 2.4Synthesis of Alkenyl Oxazolines and Oxazolinyl Oxazetidines 2.5Synthesis of Oxazolinyl Aziridines 2.6Vicarious Nucleophilic Substitution Reactions of (Chloroalkyl)oxazolines: Synthesis of (Nitrobenzyl)oxazolines and Dinitrophenyl(dioxazolinyl)ethenes 3Lithiated Oxazolinyloxiranes: Generation and Reactions 3.1Generation and Reactions of α-Lithiated Oxazolinyloxiranes 3.2Synthesis of Oxazolinylaryl Alkanones 3.3Synthesis of Allylic Alcohols from Oxazolinyloxiranes 3.4Isomerization of Oxazolinyl Allylic Alcohols: Synthesis of 3-Alkylidene-2-iminooxetanes 3.5Reactions of Lithiated Oxazolinyloxiranes with Nitrones: Synthesis of α-Epoxy γ-Amino Acids 3.6Reactions of Lithiated Oxazolinyloxiranes with α,β-Unsaturated Fischer Carbene Complexes: Synthesis of Cyclopropyl-Fused γ-Butyrolactones 3.7On the Stereochemistry of α-Lithiated Oxazolinyloxiranes 3.8Synthesis of Optically Active ortho -Sulfinylphenyl Oxazolinyl Epoxy Alcohols 3.9α-Lithiated Benzothiazolyloxiranes 3.10α-Lithiated Benzotriazolyloxiranes 3.11Synthesis of α,β–Epoxy-γ-butyrolactones from β-Lithiated Oxazolinyloxiranes 3.12Synthesis of α,β-Epoxy-γ-amino acids and α,β-Epoxy-γ-butyrolactams 3.13Synthesis of Polysubstituted Oxazolinyl Cyclopropanes 3.14Lithiation Of Terminal Oxazolinyloxirane: Synthesis of Trisubstituted Oxazolinyloxiranes and an ( E )-1,4-Dioxazolinyl-1,4-diphenylbut-2-ene-1,4-diol 4Lithiated Oxazolinyl Aziridines 4.1α-Lithiated N-Alkyl(aryl)oxazolinylaziridines: Synthesis of Aziridinolactones 4.2Lithiation of N -Alkyl Terminal Aziridines 4.3Lithiation of Heterosubstituted Oxazolinylaziridines 4.4Lithiation of N -Sulfonyl- and N -Phosphinylaziridines 5Concluding Remarks" @default.
- W2003147006 created "2016-06-24" @default.
- W2003147006 creator A5018568219 @default.
- W2003147006 date "2013-07-18" @default.
- W2003147006 modified "2023-09-27" @default.
- W2003147006 title "ChemInform Abstract: α-Lithiated α-Heterosubstituted 2-Alkyloxazolines: Key Players in Organic Synthesis" @default.
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- W2003147006 doi "https://doi.org/10.1002/chin.201332238" @default.
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