Tetrahedron Letters p. 9085 - 9086 (1996)
Update date:2022-08-04
Topics:
Andres, Celia
Duque-Soladana, J. Pablo
Iglesias, Jesus M.
Pedrosa, Rafael
N-acryloyl-2-(phenylselenomethyl)-tetrahydro-1,3-oxazine 1 generates a carbon-centred radical in the presence of tri-n-butyltin hydride and AIBN. This radical underwent diastereoselective 5-exo-trig cyclisation leading to a mixture of five-membered lactams 2a and 2b (d.e. 68%). Chromatographic separation of the diastereomers and elimination of the chiral auxiliary provided enantiopure (R)-3-methylpyrrolidine in good chemical yield. Copyright (C) 1996 Elsevier Science Ltd.
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