Topics in stereochemistry.
שמור ב:
| מחברים אחרים: | , |
|---|---|
| פורמט: | סדרון |
| שפה: | English |
| יצא לאור: |
New York :
John Wiley & Sons [etc.],
1967-.
|
| סדרה: | Topics in sterochemistry ;
v.12. |
| נושאים: | |
| גישה מקוונת: | http://dx.doi.org/10.1002/0471224499 |
תוכן הענינים:
- 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(ή-arene)chromium Complexes
- IX.Other Transformations
- X.Conclusions
- Acknowledgement
- References
- 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.ά-Amino Acid Ester Derived Enolates
- B.ά-Amino Acid Oxazolidinone Enolates
- C.ά-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
- 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: ή1 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: ή3 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
- Contents note continued: II.Generation of ά-Lithiated Oxirancs
- III.Silyl Oxiranyllithiums
- IV.Sulfonyl Oxiranyllithiums
- V.ά-Lithiated Aryloxiranes
- VI.ά-Trifluoromethyl- and Ester-Stabilized Oxiranyllithiums
- VII.Alkyl-Substituted Oxiranyllithiums
- VIII.Oxiranyllithiums by Desulfinylation
- IX.Oxiranyllithiums by Transmetalation
- X.ά-Lithiated Oxazolinyloxiranes
- XI.ά-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
- 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 ά 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 ά to a Nitrogen Atom
- 1.Cyclic Substrates
- 2.Acyclic Substrates
- C.Deprotonation ά to a Sulfur or a Phosphorus Atom
- 1.Deprotonation in ά-Position to a Sulfur Atom
- 2.Deprotonation in ά-Position to a Phosphorus Atom
- D.Deprotonation ά to a Carbon Atom
- 1.Without a Remote Coordinating Moiety
- 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 ά-Oxygen Atom
- C.Carbanions with an ά-Sulfur or Selenium Atom
- D.Carbanions with an ά-Nitrogen Atom
- E.Carbanions with Additional Stereogenic Elements.