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(−)-Sparteine-Mediated Asymmetric Cyclocarbolithiation of Alkenes Combined with a Stereospecificretro-[1,4]-Brook Rearrangement
- Source :
- Helvetica Chimica Acta. 82:2413-2424
- Publication Year :
- 1999
- Publisher :
- Wiley, 1999.
-
Abstract
- A novel domino-type reaction sequence consisting of an enantioselective intramolecular carbolithiation of 6-phenylhex-5-enyl carbamates and a highly stereospecific retro-[1,4]-Brook rearrangement is reported. The carbocycles are formed with high enantiomeric (er >98 : 2) and diastereoisomer ratios (dr >99 : 1) in good yields (47 – 60%). On the basis of the absolute configuration of the cyclization products, a stereoretentive mechanism is proposed for the retro-[1,4]-Brook rearrangement.
- Subjects :
- Chemistry
Stereochemistry
Organic Chemistry
Sparteine
Absolute configuration
Diastereomer
Enantioselective synthesis
Brook rearrangement
Biochemistry
Catalysis
Inorganic Chemistry
Stereospecificity
Intramolecular force
Drug Discovery
medicine
Physical and Theoretical Chemistry
Enantiomer
medicine.drug
Subjects
Details
- ISSN :
- 15222675 and 0018019X
- Volume :
- 82
- Database :
- OpenAIRE
- Journal :
- Helvetica Chimica Acta
- Accession number :
- edsair.doi...........67348dc6544ee6bbc9b17587dc1c1f8d