title: A General, Enantioselective Synthesis of 1-Azabicyclo[m.n.0]alkane Ring Systems.
abstract: In this Letter, we describe a novel approach for the general and enantioselective synthesis of a diverse array of small to large 1-azabicyclo[m.n.0]alkyl ring systems with an embedded olefin handle for further functionalization. The stereochemistry is established via a highly diastereoselective indium-mediated allylation of an Ellman sulfinimine in greater than 9:1 dr., which is readily separable by column chromatography to afford a single diastereomer. This methodology allows for the rapid preparation of 1-azabicyclo[m.n.0]alkane ring systems that are not readily accessible through any other chemistry in excellent overall yields and, for many systems, the only enantioselective preparation reported to date.
authors: Department of Chemistry, Vanderbilt University, Nashville, TN 37232, USA.
authors: Timothy J
authors: TJ
authors: Senter
authors: Michael L
authors: ML
authors: Schulte
authors: Leah C
authors: LC
authors: Konkol
authors: Tyler E
authors: TE
authors: Wadzinski
authors: Craig W
authors: CW
authors: Lindsley
keywords: alkaloid; allylation; azabicycle; enantioselective; olefin metathasis