Cascade Approach to Stereoselective Polycyclic Ether Formation: Epoxides as Trapping Agents in the Transposition of Allylic Alcohols

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...

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Veröffentlicht in:	Angewandte Chemie International Edition 2013-01, Vol.52 (2), p.625-628
Hauptverfasser:	Xie, Youwei, Floreancig, Paul E.
Format:	Artikel
Sprache:	eng
Schlagworte:	Alcohols cascade reactions Cascades Catalysis Conduits Epoxy Compounds - chemistry Ethers Ethers, Cyclic - chemical synthesis Ethers, Cyclic - chemistry Formations isomerization Ketones Molecular Structure oxygen heterocycles Polycyclic Compounds - chemical synthesis Polycyclic Compounds - chemistry Propanols - chemical synthesis Propanols - chemistry rearrangement Stereoisomerism stereoselectivity Thermodynamics Trapping
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Beschreibung
Zusammenfassung:	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.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201208132