Abstract
Stereoenriched atropisomeric compounds find important applications in various areas of chemistry and their synthesis is therefore a critical research target. This chapter presents a selection of the best methods available to date for the asymmetric preparation of atropisomeric compounds using dynamic stereoselective techniques. For the more common (hetero)biaryls, the selected reactions are classified according to the conformational stability of the substrates, i.e. whether they are freely rotating or are configurationally stable and require a chemically induced, temporary lowering of their rotation barrier before an asymmetric transformation can lock the axial chirality again. Strategies towards the stereoselective synthesis of non-biaryl atropisomers using dynamic resolution techniques are also covered. 'Figure Presented'.
| Original language | English |
|---|---|
| Title of host publication | Science of Synthesis |
| Editors | M.C. Bagley |
| Publisher | Georg Thieme Verlag |
| Chapter | 12 |
| Pages | 441-483 |
| Number of pages | 43 |
| Edition | 4 |
| ISBN (Electronic) | 9783132453777 |
| ISBN (Print) | 9783132453791 |
| DOIs | |
| Publication status | Published - 2023 |
Publication series
| Name | Science of Synthesis |
|---|---|
| Volume | 4 |
| ISSN (Print) | 2510-5469 |
| ISSN (Electronic) | 2566-7297 |
Bibliographical note
Publisher Copyright:© 2023 Thieme. All rights reserved.
Keywords
- amides
- asymmetric catalysis
- asymmetric synthesis
- atropisomers
- biaryls
- chiral auxiliaries
- conformation
- diastereoselectivity
- DKR
- DYKAT
- dynamic kinetic asymmetric transformation
- dynamic kinetic resolution
- dynamic thermodynamic resolution
- enantioselectivity
- nitrogen heterocycles
- organocatalysis
- palladium