Cascade Approach to Stereoselective Polycyclic Ether Formation: Epoxides as Trapping Agents in the Transposition of Allylic Alcohols
Identifieur interne : 000F23 ( Istex/Checkpoint ); précédent : 000F22; suivant : 000F24Cascade Approach to Stereoselective Polycyclic Ether Formation: Epoxides as Trapping Agents in the Transposition of Allylic Alcohols
Auteurs : Youwei Xie [États-Unis] ; Paul E. Floreancig [États-Unis]Source :
- Angewandte Chemie International Edition [ 1433-7851 ] ; 2013-01-07.
English descriptors
- KwdEn :
- Absolute stereochemistry, Allylic, Allylic alcohol, Allylic alcohol transposition, Allylic alcohols, Angew, Angewandte communications, Bidirectional stereogenesis, Cascade, Cascade reactions, Catalyst, Chem, Epoxide, Epoxide group, Epoxide opening, Equilibration, Hydroxy group, Ketone, Molecular complexity, Reaction conditions, Rhenium, Rhenium oxide, Room temperature, Single stereoisomer, Stereochemical, Stereochemical conduits, Stereochemical equilibration, Stereochemical information, Stereogenic centers, Thermodynamic control, Transposing alcohol, Transposing alcohols, Transposition, Verlag gmbh, Weinheim angew.
- Teeft :
- Absolute stereochemistry, Allylic, Allylic alcohol, Allylic alcohol transposition, Allylic alcohols, Angew, Angewandte communications, Bidirectional stereogenesis, Cascade, Cascade reactions, Catalyst, Chem, Epoxide, Epoxide group, Epoxide opening, Equilibration, Hydroxy group, Ketone, Molecular complexity, Reaction conditions, Rhenium, Rhenium oxide, Room temperature, Single stereoisomer, Stereochemical, Stereochemical conduits, Stereochemical equilibration, Stereochemical information, Stereogenic centers, Thermodynamic control, Transposing alcohol, Transposing alcohols, Transposition, Verlag gmbh, Weinheim angew.
Abstract
Complexity from simplicity: Polycyclic ethers are synthesized by cascade reactions involving the use of epoxides as electrophilic traps in the transposition of allylic alcohols. Stereogenic centers are created by functionalizing prochiral sites under thermodynamic control, and remote stereoinduction can be achieved through the use of ketones as conduits.
Url:
DOI: 10.1002/anie.201208132
Affiliations:
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<front><div type="abstract">Complexity from simplicity: Polycyclic ethers are synthesized by cascade reactions involving the use of epoxides as electrophilic traps in the transposition of allylic alcohols. Stereogenic centers are created by functionalizing prochiral sites under thermodynamic control, and remote stereoinduction can be achieved through the use of ketones as conduits.</div>
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