A General, Enantioselective Synthesis of 1-Azabicyclo[.0]alkane Ring Systems.

Senter TJ, Schulte ML, Konkol LC, Wadzinski TE, Lindsley CW
Tetrahedron Lett. 2013 54 (13): 1645-1648

PMID: 23459400 · PMCID: PMC3580858 · DOI:10.1016/j.tetlet.2013.01.041

In this Letter, we describe a novel approach for the general and enantioselective synthesis of a diverse array of small to large 1-azabicyclo[.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[.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.

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