Synthesis of benzannulated [5,6] oxa-fused/spiro-lactones via [4+2] cycloaddition with quinone methides: new insights into deconjugated butenolide reactivity
| Title | Synthesis of benzannulated [5,6] oxa-fused/spiro-lactones via [4+2] cycloaddition with quinone methides: new insights into deconjugated butenolide reactivity |
| Publication Type | Journal Article |
| Year of Publication | 2025 |
| Authors | Kumar, M, Kale, SB, Jawahar, S, Barkade, AD, Das, U |
| Journal | Journal of Organic Chemistry |
| Volume | 90 |
| Issue | 43 |
| Pagination | 15185-15190 |
| Date Published | OCT |
| Type of Article | Article |
| ISSN | 0022-3263 |
| Abstract | In this study, we unfold a Lewis-acid-catalyzed inverse electron demand hetero Diels-Alder (IEDHDA) [4 + 2] reaction, leveraging the unique beta-selective nucleophilicity of deconjugate lactone in conjunction with quinone methides for the synthesis of polycyclic fused and spiro acetals in a one-pot process. This cascade annulation reaction efficiently generates 3/4 chiral centers with high diastereoselectivity. The developed methodology proceeds under mild reaction conditions and exhibits a broad substrate scope for fused and spiro acetal formation. |
| DOI | 10.1021/acs.joc.5c01468 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.3 |
Divison category:
Organic Chemistry
Database:
Web of Science (WoS)
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