- Diastereoselective functionalizations of enecarbamates derived from pipecolic acid towards 5-guanidinopipecolates as arginine mimetics
-
Various substituents could be diastereoselectively introduced into the 5-position of pipecolic acid via electrophilic or free-radical-initiated addition to the carbon-carbon double bond of endocyclic enecarbamates derived from pipecolic acid. This study a
- Le Corre, Laurent,Kizirian, Jean-Claude,Levraud, Camille,Boucher, Jean-Luc,Bonnet, Veronique,Dhimane, Hamid
-
experimental part
p. 3388 - 3398
(2009/02/05)
-
- Palladium-catalyzed intramolecular chloroamination of alkenes
-
A mild and facile Pd-catalyzed intramolecular chloroamination of unactivated alkenes has been described. This reaction takes place at room temperature and is tolerant of synthetically useful acid-sensitive functional groups. Generally high exo-selectiviti
- Michael, Forrest E.,Sibbald, Paul A.,Cochran, Brian M.
-
supporting information; experimental part
p. 793 - 796
(2009/04/06)
-
- The Cyclization of Hex-5-enylcarbamates and Related Compounds with Benzeneselenyl chloride and Some Reactions of the 2-Substituted Piperidine Products
-
The reaction of hex-5-enylcarbamates with benzeneselenyl chloride gives adducts which cyclize in the presence of silica or stannic chloride, to 2-phenylselenomethylpiperidine derivatives which are unstable, both thermally and on silica.The selenoxides also undergo a Pummerer-type reaction to form 2-acetoxy(phenylseleno)methylpiperidine systems which can be oxidatively converted into a piperidine 2-aldehyde.The selenoxides react with carbon tetrachloride in base to form a 2,2,2-trichloroethyl substituent.Both the selenoxides and the phenylseleno groups of the cyclized products can be displaced by nucleophiles.Ethy hept-6-enylcarbamate did not give a cyclic product with benzeneselenyl chloride and silica, and gave a poor yield of a hexahydroazepine with stannic chloride.Hex-5-enamide cyclized to give a lactone, rather than a lactam, product.Hex-5-enenitrile gave Ritter reaction products with benzeneselenyl chloride in acetonitrile, and a dimer in non-nucleophilic solvents.
- Morella, Angelo M.,Ward, A. David
-
p. 445 - 468
(2007/10/02)
-