Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 31, Pages 9760-9763Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b03870
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Funding
- University of California
- [NSF-CHE-1464980]
- Direct For Mathematical & Physical Scien [1464980] Funding Source: National Science Foundation
- Division Of Chemistry [1464980] Funding Source: National Science Foundation
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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.
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