Kaicharla, Trinadh ; Roy, Tony ; Thangaraj, Manikandan ; Gonnade, Rajesh G. ; Biju, Akkattu T. (2016) Lewis Acid Catalyzed Selective Reactions of Donor-Acceptor Cyclopropanes with 2-Naphthols Angewandte Chemie, 128 (34). pp. 10215-10218. ISSN 00448249
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Official URL: http://doi.org/10.1002/ange.201604373
Related URL: http://dx.doi.org/10.1002/ange.201604373
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to John Wiley & Sons, Inc. |
| ID Code: | 128657 |
| Deposited On: | 03 Nov 2022 06:50 |
| Last Modified: | 03 Nov 2022 06:50 |
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