Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 34, Pages 10061-10064Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201604373
Keywords
annulations; arenes; Lewis acids; reaction mechanisms; small ring systems
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Funding
- Science and Engineering Research Board (SERB-DST), Government of India [SR/S1/OC/12/2012]
- Humboldt Foundation
- CSIR
- DST
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Lewis acid-catalyzed reactions of 2-substituted cyclopropane 1,1-dicarboxylates with 2-naphthols is reported. The reaction exhibits tunable selectivity depending on the nature of Lewis acid employed and proceed as a dearomatization/rearomatization sequence. With Bi(OTf)(3) as the Lewis acid, a highly selective dehydrative [3+2] cyclopentannulation takes place leading to the formation of naphthalene-fused cyclopentanes. Interestingly, engaging Sc(OTf)(3) as the Lewis acid, a Friedel-Crafts-type addition of 2-naphthols to cyclo-propanes takes place, thus affording functionalized 2-naphthols. Both reactions furnished the target products in high regioselectivity and moderate to high yields.
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