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Construction of protected hydroxylated pyrrolidines using nitrogen-centered radical cyclizations.

TitleConstruction of protected hydroxylated pyrrolidines using nitrogen-centered radical cyclizations.
Publication TypeConference Paper
Year of Publication2010
AuthorsZlotorzynska, M, Zhai, H, Sammis, G
Date Published2010///
PublisherAmerican 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)]