Journal
ORGANIC LETTERS
Volume 10, Issue 4, Pages 573-576Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol702844g
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- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0907936] Funding Source: National Science Foundation
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The reaction of benzofuranyldiazoacetates with 1,3-dienes catalyzed by the dirhodium tetracarboxylate Rh-2(R-DOSP)(4), generates formal [4 + 3] cycloadducts with >94% de and 91-98% ee. The reaction proceeds by a tandem cyclopropanation/Cope rearrangement followed by a stereoselective tautomerization. This methodology was extended to a formal synthesis of (+)-frondosin B.
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