Journal
ORGANIC LETTERS
Volume 17, Issue 20, Pages 5128-5131Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02665
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Funding
- NIH [R01GM088285]
- NSF [CHE-1464754]
- University of Wisconsin
- Chinese Scholarship Council
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1464754] Funding Source: National Science Foundation
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The first rhodium-catalyzed intramolecular [5 + 2] cycloaddition of 3-acyloxy 1,4-enyne and alkene was developed. The cycloaddition is highly diastereoselective in most cases. Various cis-fused bicyclo[5.3.0]decadienes were prepared stereoselectively. The chirality in the propargylic ester starting materials could be transferred to the bicyclic products with high efficiency. Electron-deficient phosphine ligand greatly facilitated the cycloaddition. Up to three new stereogenic centers could be generated. The resulting diene in the products could be hydrolyzed to enones, which allowed the introduction of more functional groups to the seven-membered ring.
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