Divergent synthesis of oxepino-phthalides and [5,5]-oxaspirolactones through [2+2+2]- and [2+3]-annulation of alkynyl alcohols with a-ynone-esters
| Title | Divergent synthesis of oxepino-phthalides and [5,5]-oxaspirolactones through [2+2+2]- and [2+3]-annulation of alkynyl alcohols with a-ynone-esters |
| Publication Type | Journal Article |
| Year of Publication | 2023 |
| Authors | Kambale, DA, Borade, BR, Vinodkumar, R, Kontham, R |
| Journal | Journal of Organic Chemistry |
| Volume | 88 |
| Issue | 17 |
| Pagination | 12597-12612 |
| Date Published | AUG |
| Type of Article | Article |
| ISSN | 0022-3263 |
| Abstract | Unmasking the synthetic potential of alkyne functional group of alkynyl alcohols as surrogates of carbonyl compounds, herein we present the first Bronsted acid (TfOH)-catalyzed [2 + 2 + 2]-annulation of 4-pentyn-1-ols (possessing terminal alkyne) with a-ynone-esters to access tricyclic tetrahydro-oxepino-phthalides. Besides, an unprecedented synthesis of a-acetoaryl or a-alkynyl [5,5]-oxaspirolactones has been demonstrated by employing 4-pentyn-1-ols (possessing an internal alkyne) as an annulation partner, which proceeds through a divergent [2 + 3]-annulation pathway. |
| DOI | 10.1021/acs.joc.3c01301 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.6 |
Divison category:
Organic Chemistry
Database:
Web of Science (WoS)
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