Lewis Acid Catalyzed Selective Reactions of Donor–Acceptor Cyclopropanes with 2‐Naphthols |
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| Authors: | Trinadh Kaicharla Tony Roy Manikandan Thangaraj Dr. Rajesh G. Gonnade Dr. Akkattu T. Biju |
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| Affiliation: | 1. http://academic.ncl.res.in/at.biju;2. Organic Chemistry Division, CSIR-National Chemical Laboratory, Pune-, India;3. Academy of Scientific and Innovative Research (AcSIR), New Delhi, India;4. Centre for Materials Characterization, CSIR-National Chemical Laboratory, Pune-, India |
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| Abstract: | 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 cyclopropanes 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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| Keywords: | annulations arenes Lewis acids reaction mechanisms small ring systems |
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