Lewis acid catalyzed selective reactions of donor-acceptor cyclopropanes with 2-naphthols
| Title | Lewis acid catalyzed selective reactions of donor-acceptor cyclopropanes with 2-naphthols |
| Publication Type | Journal Article |
| Year of Publication | 2016 |
| Authors | Kaicharla, T, Roy, T, Thangaraj, M, Gonnade, RG, Biju, AT |
| Journal | Angewandte Chemie-International Edition |
| Volume | 55 |
| Issue | 34 |
| Pagination | 10061-10064 |
| Date Published | AUG |
| Keywords | annulations; arenes; Lewis acids; reaction mechanisms; small ring systems |
| 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 cyclo-propanes takes place, thus affording functionalized 2-naphthols. Both reactions furnished the target products in high regioselectivity and moderate to high yields. |
| DOI | 10.1002/anie.201604373 |
| Funding Agency | Council of Scientific & Industrial Research (CSIR) - India |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 11.709 |