SmI2/water/amine mediates cleavage of allyl ether protected alcohols: application in carbohydrate synthesis and mechanistic considerations.
[reaction: see text]. SmI2/H2O/amine provides selective cleavage of unsubstituted allyl ethers in good to excellent yields. This method is therefore useful in deprotection of alcohols and carbohydrates.
Dahlén
Anders
A
Department of Chemistry, Göteborg University, SE-412 96 Göteborg, Sweden.
Sundgren
Andreas
A
Lahmann
Martina
M
Oscarson
Stefan
S
Hilmersson
Göran
G
D000438:Alcohols / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry; D002384:Catalysis; D004987:Ethers / Q000737:chemistry*; D005021:Ethylamines / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D010647:Phenyl Ethers / Q000737:chemistry; D011437:Propylamines / Q000737:chemistry; D012493:Samarium / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D000438:Alcohols; D000498:Allyl Compounds; D000588:Amines; D002241:Carbohydrates; D004987:Ethers; D005021:Ethylamines; D007454:Iodides; D010647:Phenyl Ethers; D011437:Propylamines; D014867:Water; C076695:phenyl allyl ether; D012493:Samarium; C409809:samarium diiodide; C035263:2-propylamine; C016162:triethylamine