Overcoming product inhibition in catalysis of the intramolecular Schmidt reaction
A method for carrying out the intramolecular Schmidt reaction of alkyl azides and ketones using a substoichiometric amount of catalyst is reported. Following extensive screening, the use of the strong hydrogen-bond-donating solvent hexafluoro-2-propanol was found to be consistent with low catalyst loadings, which ranged from 2.5 mol % for favorable substrates to 25 mol % for more difficult cases. Reaction optimization, broad substrate scope, and preliminary mechanistic studies of this improved version of the reaction are described.
Regioselective synthesis of piperidinones by metal catalyzed ring expansion-carbonylation reactions. Remarkable cobalt and/or ruthenium carbonyl catalyzed rearrangement and cyclization reactions
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De Wang,Alper
p. 7018 - 7024
(2007/10/02)
Cyclic Allylamine-Enamine Systems. Part 8. Isomerisation Using Rhodium Complexes. 3-Aminoalkylidene-3H-indoles. Part 5. 6,7-Dihydroindoloquinolizine and 1,2,3,4,6,7-Hexahydroindoloquinolizine
The use of rhodium-complex catalysis for cyclic allylamine --> cyclic enamine isomerisation is described.Indoloquinolizines are produced using this methodology and also via 3-amino-3H-indole intermediates.N-alkylation of N-silylated amides is described.
Salas, Marisa,Al-Khawaja, Ibtisam K.,Thomas, Michelle J.,Joule, John A.
p. 1666 - 1675
(2007/10/02)
THE PHOTOCHEMICAL OR THERMAL REARRANGEMENT OF OXAZIRANES AS A METHOD IN ALKALOID SYNTHESIS
The conversion of cyclic ketones to β-arylethyl amine derived imines, their oxidation to oxaziranes and subsequent photochemical rearrangement to N-(β-arylethyl) lactams was probed as a potential method for alkaloid syntheses.
Kuehne, Martin E.,Parsons, W. H.
p. 3763 - 3766
(2007/10/02)
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