Rapid and stereoselective synthesis of spirocyclic ethers via the intramolecular Piancatelli rearrangement.
The first example of a Piancatelli rearrangement of alcohols is demonstrated utilizing dysprosium(III) triflate as a catalyst to access oxaspirocycles in a highly diastereoselective manner. The cascade reaction constructs the spirocyclic ether ring system and the tertiary stereocenter in a single operation and is experimentally easy to perform.
Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106-9510, USA.
Leoni I
LI
Palmer
Javier Read
JR
de Alaniz
D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D004987:Ethers; D005663:Furans; D013141:Spiro Compounds