321903-47-3Relevant articles and documents
Tributyltin hydride-mediated radical cyclisation of carbonyls to form functionalised oxygen and nitrogen heterocycles
Bentley, Jon,Nilsson, Paul A.,Parsons, Andrew F.
, p. 1461 - 1469 (2007/10/03)
The tributyltin hydride-mediated cyclisation of unsaturated ethers and amines bearing an aldehyde or α,β-unsaturated ketone group is reported. Cyclisation proceeds via reversible addition of the tributyltin radical to the carbonyl double bond to form an intermediate O-stannyl ketyl. This nucleophilic radical can add intramolecularly to electron-rich double bonds to form substituted 5- or 6-membered rings. The efficiency of the cyclisation to form, for example, hydroxytetrahydrofurans, chromanols or quinolones, is shown to depend on the nature of the acceptor double bond and also on the stability of the intermediate O-stannyl ketyl. Thus, resonance-stabilised allylic or benzylic O-stannyl ketyl radicals have been shown, for the first time, to have a particular application in slow radical cyclisations leading to butyrolactones or pyrans.
Tributyltin hydride-mediated radical cyclisation of aldehydes and unsaturated ketones: The synthesis of hydroxy tetrahydrofurans, chromanols and related compounds
Bebbington, David,Bentley, Jon,Nilsson, Paul A.,Parsons, Andrew F.
, p. 8941 - 8945 (2007/10/03)
The tributyltin hydride-mediated cyclisation of unsaturated ethers bearing an aldehyde or α,β-unsaturated ketone group is reported. Cyclisation proceeds via addition of the tributyltin radical to the carbonyl double bond and the resultant O-stannyl ketyl can add intramolecularly to electron-rich double bonds to form hydroxy tetrahydrofurans, chromanols or related compounds. (C) 2000 Elsevier Science Ltd.
