Stereospecific Intramolecular Reductive Cross-Electrophile Coupling Reactions for Cyclopropane Synthesis

The stereo­specific reductive cross-electro­phile coupling reaction of 2-aryl-4-chloro­tetra­hydro­pyrans to afford disubstituted cyclo­propanes is reported. This ring contraction presents surprises with respect to the stereo­chemical outcome of reaction of the alkyl halide moiety. While cross-coupl...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-08, Vol.137 (31), p.9760-9763
Main Authors: Tollefson, Emily J, Erickson, Lucas W, Jarvo, Elizabeth R
Format: Article
Language:English
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Summary:The stereo­specific reductive cross-electro­phile coupling reaction of 2-aryl-4-chloro­tetra­hydro­pyrans to afford disubstituted cyclo­propanes is reported. This ring contraction presents surprises with respect to the stereo­chemical outcome of reaction of the alkyl halide moiety. While cross-coupling and reductive cross-electro­phile coupling reactions of alkyl halides are typically stereo­ablative, using a chiral catalyst to set the stereo­center, this transformation proceeds with high stereo­chemical fidelity at the alkyl halide and ether bearing stereo­genic centers. This approach provides straightforward access to highly substituted cyclopropanes in two steps from commercially available aldehydes.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b03870