| Description |
volumes ; 24 cm |
| Series |
Topics in sterochemistry ; v.12 |
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Topics in sterochemistry ; v.12
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| Contents |
Machine generated contents note: ch. 1 Asymmetric Deprotonations Using Chiral Lithium Amide Bases / Michael D. Weller -- I.Introduction -- II.Enantioselective Conversion of Epoxides into Allylic Alcohols -- III.Enantioselective Deprotonations Adjacent to Sulfur -- IV.Enantioselective Deprotonation of Cyclic Prochiral Ketones -- A.Methodology Developments -- B.Applications of Chiral Lithium Amides in Synthesis -- 1.Deprotonations of Substituted Monocyclic Cyclohexanones -- 2.Deprotonations of Bicyclic Cyclohexanones -- 3.Deprotonations of Cycloheptanones and Cyclooctanones -- V.Desymmetrisation of Cyclic Imides -- VI.Enantioselective Deprotonation at Bridgehead Carbons -- VII.Kinetic Resolution Processes -- VIII.Enantioselective Deprotonation of Tricarbonyl(η-arene)chromium Complexes -- IX.Other Transformations -- X.Conclusions -- Acknowledgement -- References -- |
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Contents note continued: ch. 2 Self-Regeneration of Stereocenters (SRS) via Stereolabile Axially Chiral Intermediates / Stephanie Antolak Bryson -- I.Introduction -- II.Kinetic Requirements for SRS via Stereolabile Axially Chiral Intermediates -- III.SRS via Stereolabile Axially Chiral Enolates -- A.α-Amino Acid Ester Derived Enolates -- B.α-Amino Acid Oxazolidinone Enolates -- C.α-Amino Acid-Derived 1,4-Benzodiazepine Enolates -- IV.SRS via Stereolabile Axially Chiral Alkenyl Gold Carbocation Intermediates -- V.SRS via Stereolabile Axially Chiral Diradical Intermediates -- VI.Concluding Remarks -- Acknowledgement -- Note Added in Proof -- References -- ch. 3 Overview of Carbanion Dynamics and Electrophilic Substitutions in Chiral Organolithium Compounds / Robert E. Gawley -- I.Introduction -- II.The Carbon-Lithium Bond -- III.Chiral Organolithiums -- IV.Methods of Generation of Organolithiums -- A.Asymmetric Deprotonations -- B.Tin-Lithium Exchange -- |
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Contents note continued: V.Carbanion Dynamics -- VI.Relative Rates: Inversion vs. Substitution -- A.Fast Inversion -- B.Slow Inversion -- VII.Enantiomerization Dynamics -- A.Benzylic Organolithiums -- B.Nonbenzylic Organolithiums -- C.Heteroatom Stabilized Organolithiums -- D.Diastereomeric Bias -- VIII.Dynamic Resolutions -- A.Dynamic Thermodynamic Resolutions -- B.Dynamic Kinetic Resolutions -- C.Competing Inversion and Substitution: The Hoffmann Test -- IX.Steric Course of Electrophilic Substitutions: η1 Organolithiums -- A.Examples of SE2inv -- B.Examples of SE2ret -- C.Examples of SET -- D.Implicating or Eliminating SET as a Mechanism -- X.Steric Course of Electrophilic Substitutions: η3 Organolithiums -- A.Examples of SE2inv -- B.Examples of SE2ret -- XI.Summary and Conclusions -- Acknowledgement -- References -- ch. 4 Oxiranyllithiums as Chiral Synthons for Asymmetric Synthesis / Antonio Salomone -- I.Introduction -- |
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Contents note continued: II.Generation of α-Lithiated Oxirancs -- III.Silyl Oxiranyllithiums -- IV.Sulfonyl Oxiranyllithiums -- V.α-Lithiated Aryloxiranes -- VI.α-Trifluoromethyl- and Ester-Stabilized Oxiranyllithiums -- VII.Alkyl-Substituted Oxiranyllithiums -- VIII.Oxiranyllithiums by Desulfinylation -- IX.Oxiranyllithiums by Transmetalation -- X.α-Lithiated Oxazolinyloxiranes -- XI.α-Lithiated Benzotriazolyloxiranes -- XII.Conclusions -- References -- ch. 5 Test on the Configurational Stability/Lability of Organolithium Compounds / Reinhard W. Hoffmann -- I.Introduction -- II.Configurational Stability -- III.The Test, Historic Development -- IV.The Test -- V.Variants of the Test -- VI.Application of the Test to the Configurational Stability of Organometallic Species -- VII.Application of the Test to Other Mechanistic Problems -- VIII.Alternative Approaches -- IX.Concluding Remarks -- Acknowledgement -- References -- |
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Contents note continued: ch. 6 Mechanism and Stereochemical Features in Asymmetric Deprotonation Using RLi/(-)-Sparteine Bases / Jean-Claude Kizirian -- I.Introduction -- II.Deprotonation: Regioselectivity and Mechanism -- III.Configurational Stability of Lithiated Species -- IV.X-Ray Structure of RLi/(-)-Sparteine Complexes -- V.Deprotonation Using RLi/(-)-Sparteine as Base -- A.Deprotonation α to an Oxygen Atom -- 1.Hoppe's Alkyl Carbamates -- 2.Hoppe's Aryl Carbamates -- 3.Hoppe's Vinyl Carbamates -- 4.Hoppe's Propargyl Carbamates -- 5.Benzylic, Allylic and Propargylic Ethers -- 6.Epoxides -- B.Deprotonation α to a Nitrogen Atom -- 1.Cyclic Substrates -- 2.Acyclic Substrates -- C.Deprotonation α to a Sulfur or a Phosphorus Atom -- 1.Deprotonation in α-Position to a Sulfur Atom -- 2.Deprotonation in α-Position to a Phosphorus Atom -- D.Deprotonation α to a Carbon Atom -- 1.Without a Remote Coordinating Moiety -- |
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Contents note continued: 2.With a Remote Coordinating Moiety -- VI.Conclusions -- References -- ch. 7 Dynamic Resolutions of Chiral Organolithiums / Nadeem S. Sheikh -- I.Introduction -- II.Rates of Interconversion of Chiral Organolithiums -- III.Theory of Dynamic Resolutions -- A.Dynamic Thermodynamic Resolution -- B.Dynamic Kinetic Resolution -- C.Crystallization-Induced Dynamic Resolution -- IV.Examples of Dynamic Resolutions -- A.Benzylic and Allylic Carbanions -- B.Carbanions with an α-Oxygen Atom -- C.Carbanions with an α-Sulfur or Selenium Atom -- D.Carbanions with an α-Nitrogen Atom -- E.Carbanions with Additional Stereogenic Elements |
| Analysis |
Stereochemistry Serials |
| Notes |
Editors: v. 1- N. L. Allinger and E. L. Eliel |
| Bibliography |
Includes bibliographical references and index |
| Event |
Editors: v. 1- N. L. Allinger and E. L. Eliel |
| Notes |
Also issued online |
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Mode of access: World Wide Web |
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Current Copyright Fee: GBP17.00 0 Uk |
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Indexed selectively by: Chemical abstracts 0009-2258 |
| Has Indexes |
Vols. 1-4, 1967-69, in v. 4; Vols. 1-5, in v. 5 |
| Issuing Body |
Editors: v. 1- N. L. Allinger and E. L. Eliel |
| Subject |
Philosophy.
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Stereochemistry.
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Religion.
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Chemistry, Physical.
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| Genre/Form |
Periodical.
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Periodicals.
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Periodicals.
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| Author |
Eliel, Ernest L. (Ernest Ludwig), 1921-2008, editor
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Allinger, Norman L., editor
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| LC no. |
67013943 |
| ISSN |
0082-500X |
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