Intramolecular Cascade Cyclization of Cyclobutanone: Asymmetric Construction of Cyclobutanone Fused Oxa-Spirocycles.
| Title: | Intramolecular Cascade Cyclization of Cyclobutanone: Asymmetric Construction of Cyclobutanone Fused Oxa-Spirocycles. |
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| Authors: | Panda S; Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, Bhopal By-pass Road, Bhauri, Bhopal 462066, India.; Chavan ND; Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, Bhopal By-pass Road, Bhauri, Bhopal 462066, India.; Ghorai P; Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, Bhopal By-pass Road, Bhauri, Bhopal 462066, India. |
| Source: | Organic letters [Org Lett] 2025 Jan 17; Vol. 27 (2), pp. 541-545. Date of Electronic Publication: 2025 Jan 08. |
| Publication Type: | Journal Article |
| Language: | English |
| Journal Info: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 100890393 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1523-7052 (Electronic) Linking ISSN: 15237052 NLM ISO Abbreviation: Org Lett Subsets: MEDLINE; PubMed not MEDLINE |
| Imprint Name(s): | Original Publication: Washington, DC : American Chemical Society, c1999- |
| Abstract: | The successful implementation of a cascade reaction involving a cyclobutyl unit has posed a significant challenge in achieving ring-retentive functionalization because of the ring's sacrificial tendency. Herein, we have accomplished a cinchona-derived squaramide-catalyzed cascade reaction sequence, encompassing the desymmetrization of cyclobutanone, followed by an aldol reaction and, subsequently, a 1,4-addition step. This overall process offers a viable strategy to access architecturally fascinating oxa-spirocycles fused with cyclobutanone motifs in good yields with high optical purity. |
| Entry Date(s): | Date Created: 20250108 Latest Revision: 20250117 |
| Update Code: | 20260130 |
| DOI: | 10.1021/acs.orglett.4c03593 |
| PMID: | 39772593 |
| Database: | MEDLINE |
Journal Article