198290-25-4Relevant academic research and scientific papers
Radical promoted cyclisations of trichloroacetamides with silyl enol ethers and enol acetates: The role of the hydride reagent [tris(trimethylsilyl)silane vs. tributylstannane]
Quirante, Josefina,Escolano, Carmen,Diaba, Faiza,Bonjoch, Josep
, p. 1157 - 1162 (1999)
Reactions between 1-(carbamoyl)dichloromethyl radicals and electron-rich alkenes acting as radical acceptors are reported for the first time. The intramolecular reaction of trichloroacetamides with silyl enol ethers gives ketones using (TMS)3SiH as the mediator, and alcohols when using Bu3SnH. The reaction with enol acetates gives acetates using either of the above hydride reagents. These radical processes have been applied to the synthesis of 2-azabicyclo[3.3.1]nonanes.
Cyclization of 1-(carbamoyl)dichloromethyl radicals upon activated alkenes. A new entry to 2-azabicyclo[3.3.1]nonanes
Quirante, Josefina,Escolano, Carmen,Costeja, Laura,Bonjoch, Josep
, p. 6901 - 6904 (1997)
The synthesis of 2-azabicyclo[3.3.1]nonanes using a radical cyclization process as the piperidine ring-forming step is described. The reaction involves 1-(carbamoyl)dichloromethyl radicals which react intramolecularly with simple or activated alkenes, such as enol acetates or silyl enol ethers.
A radical route to morphans. Synthesis and spectroscopic data of the 2- azabicyclo[3.3.1]Nonane
Quirante, Josefina,Escolano, Carmen,Diaba, Fa?za,Bonjoch, Josep
, p. 731 - 738 (2007/10/03)
The synthesis of 1-benzyl-2-azabicyclo[3.3.1]nonan-3-one (8) through radical cyclization, involving an intramolecular addition of a carbamoyl- dichloromethyl radical upon an alkene, is described. Conversion of 8 to the morphan itself, and the spectroscopic analysis of some derivatives of this series are reported.
