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    Organolithiums: Selectivity for Synthesis (Tetrahedron Organic Chemistry) (Hardback) By (author) Jonathan Clayden

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    DescriptionThis volume, number 23 in the "Tetrahedron Organic Chemistry" series, presents organolithium chemistry from the perspective of a synthetic organic chemist, drawing from the synthetic literature to present a unified overview of how organolithiums can be used to make molecules. The development of methods for the regioselective synthesis of organolithiums has replaced their image of indiscriminate high reactivity with one of controllable and subtle selectivity. Organolithium chemistry has a central role in the selective construction of C-C bonds in both simple and complex molecules, and for example has arguably overtaken aromatic electrophilic substitution as the most powerful method for regioselective functionalisation of aromatic rings. The twin themes of reactivity and selectivity run through the book, which reviews the ways by which organolithiums may be formed and the ways in which they react. Topics include advances in directed metallation, reductive lithiation and organolithium cyclisation reactions, along with a discussion of organolithium stereochemistry and the role played by ligands such as (-)-sparteine.


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  • Full bibliographic data for Organolithiums

    Title
    Organolithiums
    Subtitle
    Selectivity for Synthesis
    Authors and contributors
    By (author) Jonathan Clayden
    Physical properties
    Format: Hardback
    Number of pages: 400
    Width: 154 mm
    Height: 232 mm
    Thickness: 30 mm
    Weight: 862 g
    Language
    English
    ISBN
    ISBN 13: 9780080432625
    ISBN 10: 008043262X
    Classifications

    B&T Book Type: NF
    BIC E4L: SCI
    BIC subject category V2: TV
    Ingram Subject Code: SE
    Libri: I-SE
    B&T General Subject: 710
    B&T Modifier: Region of Publication: 04
    B&T Modifier: Academic Level: 02
    B&T Merchandise Category: POD
    Nielsen BookScan Product Class 3: S7.5
    BIC subject category V2: TDC
    Warengruppen-Systematik des deutschen Buchhandels: 16880
    BISAC V2.8: SCI013040
    LC subject heading: ,
    DC21: 547.053810459
    DC22: 547/.053810459
    LC classification: QD412.L5 C57 2002
    LC subject heading:
    DC22: 547.05381045
    LC subject heading:
    BIC subject category V2: PNND
    Thema V1.0: TDC, PNND
    Publisher
    ELSEVIER SCIENCE & TECHNOLOGY
    Imprint name
    Pergamon
    Publication date
    26 July 2002
    Publication City/Country
    Amsterdam
    Table of contents
    Introduction: scope and overview; organolithiums in solution. Regioselective synthesis of organolithiums by deprotonation: general points; lithiation alpha to heteroatoms; ortholithiation; lateral lithiation; remote lithiation, and beta-lithiation of non-aromatic compounds; superbases; co-operation, competition and regioselectivity. Regioselective synthesis of organolithiums by X-Li exchange: halogen-lithium exchange; tin-lithium exchange; chalcogen-lithium exchange; phosphorus-lithium exchange. Regioselective synthesis of organolithiums by C-X reduction: reductive lithiation of alkyl and aryl halides; reductive lithiation of C-O bonds; reductive lithiation of C-N bonds; reductive lithiation of C-S bonds; reductive lithiation of C-C bonds and pi-bonds. Stereoselective and stereospecific synthesis of organolithiums: configurational stability of organolithiums; Stereospecific synthesis of organolithiums by X-Li exchange; diastereoselective deprotonation; enantioselective deprotonation. Stereospecific and stereoselective substitution reactions of organolithiums: stereospecific reactions of organolithium compounds; stereoselective substitution in the presence of chiral ligands. Regio- and stereoselective addition reactions of organolithiums: intermolecular addition to pi bonds - carbolithiation; intramolecular addition and substitution reactions - anionic cyclization. Organolithium rearrangements: Shapiro reaction; Brook rearrangements; [1,2]-Wittig rearrangements; [2,3]-Wittig rearrangements. Organolithiums in synthesis: ochratoxin - ortholithiation and anionic Fries rearrangement; corydalic acid methyl ester - lateral lithiation; fredericamycin A - ortho, lateral and alpha-lithiation; (?)-Atpenin B - metallation of an aromatic heterocycle; flurbiprofen - metallation with LiCKOR superbases; California red scale pheromone - alpha- and reductive lithiation C1-C9 of the Bryostatins - diastereoselective bromine-lithium exchange; (S)-1-methyldodecyl acetate, a Drosophila pheromone - (-)-sparteine assisted enantioselective lithiation; (-)-Paroxetine - (-)-sparteine-promoted asymmetric lithiation and substitution.