| Title | Construction of protected hydroxylated pyrrolidines using nitrogen-centered radical cyclizations. |
| Publication Type | Conference Paper |
| Year of Publication | 2010 |
| Authors | Zlotorzynska, M, Zhai, H, Sammis, G |
| Date Published | 2010/// |
| Publisher | American Chemical Society |
| Abstract | We have developed a new nitrogen-radical cyclization onto silyl enol ethers. In the course of our synthesis of alkaloid CYB-3, we found that the cyclization diastereoselectivity was dependent on a complex combination of sterics and olefin geometry. Alkyl-and aryl-substituted substrates cyclized with high selectivity regardless of olefin geometry or substitution pattern. When electroneg. substituents were introduced adjacent to the silyl enol ether, only Z-silyl enol ethers provided high diastereoselectivities. This methodol. was also applied to the synthesis of 1,4-dideoxy-1,4-imino-L-ribitol. [on SciFinder(R)] |
