Related Experiment Videos
Sulfoxides as stereochemical controllers in intermolecular Heck reactions
N Díaz Buezo1, J C de la Rosa, J Priego
1Departamento de Química Orgánica, facultad de Ciencias, Universidad Autónoma de Madrid, Spain.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 13, 2001
Summary
This study explores chiral sulfoxides as auxiliaries in Heck reactions, achieving useful yields and asymmetric induction. The O-(N,N-dimethylamino)phenylsulfinyl group provided the best results for enantioselective synthesis.
Area of Science:
- Organic Chemistry
- Asymmetric Synthesis
- Catalysis
Background:
- Chiral auxiliaries are crucial for controlling stereochemistry in organic synthesis.
- The Heck reaction is a powerful tool for carbon-carbon bond formation.
- Developing efficient asymmetric Heck reactions remains an important goal in synthetic chemistry.
Purpose of the Study:
- To investigate substituted sulfoxides as chiral auxiliaries in intermolecular Heck reactions.
- To achieve high yields and asymmetric induction in the synthesis of substituted dihydrofurans and cyclopentenes.
- To apply these methods for the enantioselective synthesis of valuable cyclic compounds.
Main Methods:
- Utilized various substituted sulfoxides as chiral auxiliaries.
- Employed intermolecular Heck reactions involving sulfinyldihydrofurans and sulfinylcyclopentenes with iodoarenes.
- Optimized reaction conditions using [Pd(OAc)2]/Ag2CO3 and bidentate phosphine ligands.
Main Results:
- Achieved synthetically useful yields and asymmetric inductions.
- Identified the O-(N,N-dimethylamino)phenylsulfinyl group as the most effective auxiliary, yielding superior diastereoselectivities.
- Demonstrated the successful application of these sulfoxide-controlled processes for enantioselective synthesis.
Conclusions:
- Substituted sulfoxides are effective chiral auxiliaries for asymmetric intermolecular Heck reactions.
- The O-(N,N-dimethylamino)phenylsulfinyl auxiliary offers excellent stereocontrol.
- This methodology provides a viable route for the enantioselective synthesis of substituted dihydrofurans and cyclopentenes.