Synthesis of Spirocyclic 1‐Pyrrolines from Nitrones and Arynes through a Dearomative [3,3′]‐Sigmatropic Rearrangement
A dearomative [3,3′]‐sigmatropic rearrangement that converts N‐alkenylbenzisoxazolines into spirocyclic pyrroline cyclohexadienones has been developed by using the dipolar cycloaddition of an N‐alkenylnitrone and an aryne to access these unusual transient rearrangement precursors. This cascade react...
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| Published in | Angewandte Chemie International Edition Vol. 59; no. 35; pp. 15244 - 15248 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
24.08.2020
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| Edition | International ed. in English |
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| Abstract | A dearomative [3,3′]‐sigmatropic rearrangement that converts N‐alkenylbenzisoxazolines into spirocyclic pyrroline cyclohexadienones has been developed by using the dipolar cycloaddition of an N‐alkenylnitrone and an aryne to access these unusual transient rearrangement precursors. This cascade reaction affords spirocyclic pyrrolines that are inaccessible through dipolar cycloadditions of exocyclic cyclohexenones and provides a fundamentally new approach to novel spirocyclic pyrroline and pyrrolidine motifs that are common scaffolds in biologically‐active molecules. Diastereoselective functionalization processes have also been explored to demonstrate the divergent synthetic utility of the unsaturated spirocyclic products.
A cascade reaction has been designed for the synthesis of spirocyclic pyrrolines from nitrones and arynes. A key feature of this transformation is an unusual dearomative [3,3′]‐sigmatropic rearrangement of a heterocyclic intermediate that results in a spirocyclization. This modular approach provides access to three‐dimensionally‐defined pyrrolines and pyrrolidines with opportunities for divergent derivatization. |
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| AbstractList | A dearomative [3,3′]‐sigmatropic rearrangement that converts N‐alkenylbenzisoxazolines into spirocyclic pyrroline cyclohexadienones has been developed by using the dipolar cycloaddition of an N‐alkenylnitrone and an aryne to access these unusual transient rearrangement precursors. This cascade reaction affords spirocyclic pyrrolines that are inaccessible through dipolar cycloadditions of exocyclic cyclohexenones and provides a fundamentally new approach to novel spirocyclic pyrroline and pyrrolidine motifs that are common scaffolds in biologically‐active molecules. Diastereoselective functionalization processes have also been explored to demonstrate the divergent synthetic utility of the unsaturated spirocyclic products. A dearomative [3,3′]‐sigmatropic rearrangement that converts N‐alkenylbenzisoxazolines into spirocyclic pyrroline cyclohexadienones has been developed by using the dipolar cycloaddition of an N‐alkenylnitrone and an aryne to access these unusual transient rearrangement precursors. This cascade reaction affords spirocyclic pyrrolines that are inaccessible through dipolar cycloadditions of exocyclic cyclohexenones and provides a fundamentally new approach to novel spirocyclic pyrroline and pyrrolidine motifs that are common scaffolds in biologically‐active molecules. Diastereoselective functionalization processes have also been explored to demonstrate the divergent synthetic utility of the unsaturated spirocyclic products. A cascade reaction has been designed for the synthesis of spirocyclic pyrrolines from nitrones and arynes. A key feature of this transformation is an unusual dearomative [3,3′]‐sigmatropic rearrangement of a heterocyclic intermediate that results in a spirocyclization. This modular approach provides access to three‐dimensionally‐defined pyrrolines and pyrrolidines with opportunities for divergent derivatization. |
| Author | Reidl, Tyler W. Koto, Nicholas‐George Alshreimi, Abdullah S. Zhang, Guanqun Islam, Shahidul M. Peña, Ricardo L. Wink, Donald J. Anderson, Laura L. |
| Author_xml | – sequence: 1 givenname: Abdullah S. surname: Alshreimi fullname: Alshreimi, Abdullah S. organization: University of Illinois at Chicago – sequence: 2 givenname: Guanqun surname: Zhang fullname: Zhang, Guanqun organization: University of Illinois at Chicago – sequence: 3 givenname: Tyler W. surname: Reidl fullname: Reidl, Tyler W. organization: University of Illinois at Chicago – sequence: 4 givenname: Ricardo L. surname: Peña fullname: Peña, Ricardo L. organization: University of Illinois at Chicago – sequence: 5 givenname: Nicholas‐George surname: Koto fullname: Koto, Nicholas‐George organization: University of Illinois at Chicago – sequence: 6 givenname: Shahidul M. surname: Islam fullname: Islam, Shahidul M. organization: University of Illinois at Chicago – sequence: 7 givenname: Donald J. surname: Wink fullname: Wink, Donald J. organization: University of Illinois at Chicago – sequence: 8 givenname: Laura L. orcidid: 0000-0002-8764-7522 surname: Anderson fullname: Anderson, Laura L. email: lauralin@uic.edu organization: University of Illinois at Chicago |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/32374468$$D View this record in MEDLINE/PubMed |
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| Keywords | dearomatization CATALYTIC ASYMMETRIC DEAROMATIZATION dipolar cycloaddition CLAISEN REARRANGEMENT INTRAMOLECULAR DEAROMATIZATION INDOLES AMINO-ACIDS 1,3-DIPOLAR CYCLOADDITION CONSTRUCTION nitrones spirocyclic pyrroline PHENOL DEAROMATIZATION STEREOGENIC CENTERS sigmatropic rearrangement DERIVATIVES |
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| Snippet | A dearomative [3,3′]‐sigmatropic rearrangement that converts N‐alkenylbenzisoxazolines into spirocyclic pyrroline cyclohexadienones has been developed by using... A dearomative [3,3 ']-sigmatropic rearrangement that converts N-alkenylbenzisoxazolines into spirocyclic pyrroline cyclohexadienones has been developed by... A dearomative [3,3']-sigmatropic rearrangement that converts N-alkenylbenzisoxazolines into spirocyclic pyrroline cyclohexadienones has been developed by using... |
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| SubjectTerms | Cascade chemical reactions Chemistry Chemistry, Multidisciplinary Cycloaddition dearomatization dipolar cycloaddition Divergence nitrones Physical Sciences Pyrrolidine Science & Technology sigmatropic rearrangement spirocyclic pyrroline Stereoselectivity |
| Title | Synthesis of Spirocyclic 1‐Pyrrolines from Nitrones and Arynes through a Dearomative [3,3′]‐Sigmatropic Rearrangement |
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