Cationic cyclopentannelation of allene ethers.
The variant of the Nazarov cyclization that makes use of allenyl ethers is suitable for the preparation of diverse, highly functionalized cyclopentenones. Three variants of the basic reaction, differing in the nature of the electrophile that is combined with the allene to prepare the precursor for the pentadienyl cation, are described. One variant, which utilizes an alpha,beta-unsaturated morpholino amide, has been successfully employed in an enantioselective version of the cyclopentannelation.
Tius
Marcus A
MA
Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, USA. tius@gold.chem.hawaii.edu
D000498:Allyl Compounds / Q000737:chemistry*; D000577:Amides / Q000737:chemistry; D002412:Cations; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis*; D004987:Ethers / Q000737:chemistry*; D013237:Stereoisomerism
D000498:Allyl Compounds; D000577:Amides; D002412:Cations; D003517:Cyclopentanes; D004987:Ethers