Mrpn. Matos et al., Synthesis of substituted pyrrolidines by sequential radical cyclization and N-acyliminium ion reactions, TETRAHEDR L, 40(52), 1999, pp. 9189-9193
Readily available N-acyl-2-pyrrolines are converted into functionalized alp
ha-alkoxy-beta-iodopyrrolidines by N-iodosuccinimide promoted alcohol addit
ion to the enamine group. These compounds are readily cyclized using a sodi
um cyanoborohydride-catalytic tributylstannane system affording functionali
zed pyrrolidines in good yields. The cyclized products undergo N-acyliminiu
m ion reactions, such as BF3. OEt2 mediated addition of allyltrimethylsilan
e. (C) 1999 Elsevier Science Ltd. All rights reserved.