459410-20-9Relevant academic research and scientific papers
A novel, stereoselective silyl-directed stevens [1,2]-shift of ammonium ylides
Vanecko, John A.,West
, p. 2813 - 2816 (2007/10/03)
(figure presented) The silyl group of 2-silylpyrrolidines such as 1 plays several critical roles: a stereochemical control element in a facially selective carbenoid addition to the ring nitrogen, a stereochemical "placeholder" during regioselective 1,2-migration with retention by the resulting spirocyclic ammonium ylide, and a hydroxyl surrogate for an eventual stereoselective Fleming-Tamao oxidation. This chemistry represents a novel use of the Stevens rearrangement and offers a short, enantioselective route to hydroxylated quinolizidines such as 3 from Boc-pyrrolidine.
