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Stereoselective Synthesis of Fused Vinylcyclopropanes by Intramolecular Tsuji–Trost Cascade Cyclization
[Image: see text] A stereoselective intramolecular Tsuji–Trost cascade cyclization of (homo)allylic vicinal diacetates with a pendant β-ketoamide or related carbon nucleophile to give γ-lactam-fused vinylcyclopropanes is reported. In addition to two new rings, the products contain three new C–C ster...
| Autores principales: | , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2018
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6218879/ https://www.ncbi.nlm.nih.gov/pubmed/30350659 http://dx.doi.org/10.1021/acs.orglett.8b02232 |
| _version_ | 1783368538588708864 |
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| author | Braun, John Ariëns, Maxim I. Matsuo, Bianca T. de Vries, Steven van Wordragen, Ellen D. H. Ellenbroek, Brecht D. Vande Velde, Christophe M. L. Orru, Romano V. A. Ruijter, Eelco |
| author_facet | Braun, John Ariëns, Maxim I. Matsuo, Bianca T. de Vries, Steven van Wordragen, Ellen D. H. Ellenbroek, Brecht D. Vande Velde, Christophe M. L. Orru, Romano V. A. Ruijter, Eelco |
| author_sort | Braun, John |
| collection | PubMed |
| description | [Image: see text] A stereoselective intramolecular Tsuji–Trost cascade cyclization of (homo)allylic vicinal diacetates with a pendant β-ketoamide or related carbon nucleophile to give γ-lactam-fused vinylcyclopropanes is reported. In addition to two new rings, the products contain three new C–C stereocenters (two of which are quaternary) with a 9:1 dr. Moreover, the reaction proceeds in >94% enantiospecificity with optically enriched starting materials, using an inexpensive carbohydrate as the source of chirality. |
| format | Online Article Text |
| id | pubmed-6218879 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2018 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-62188792018-11-07 Stereoselective Synthesis of Fused Vinylcyclopropanes by Intramolecular Tsuji–Trost Cascade Cyclization Braun, John Ariëns, Maxim I. Matsuo, Bianca T. de Vries, Steven van Wordragen, Ellen D. H. Ellenbroek, Brecht D. Vande Velde, Christophe M. L. Orru, Romano V. A. Ruijter, Eelco Org Lett [Image: see text] A stereoselective intramolecular Tsuji–Trost cascade cyclization of (homo)allylic vicinal diacetates with a pendant β-ketoamide or related carbon nucleophile to give γ-lactam-fused vinylcyclopropanes is reported. In addition to two new rings, the products contain three new C–C stereocenters (two of which are quaternary) with a 9:1 dr. Moreover, the reaction proceeds in >94% enantiospecificity with optically enriched starting materials, using an inexpensive carbohydrate as the source of chirality. American Chemical Society 2018-10-12 2018-11-02 /pmc/articles/PMC6218879/ /pubmed/30350659 http://dx.doi.org/10.1021/acs.orglett.8b02232 Text en Copyright © 2018 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes. |
| spellingShingle | Braun, John Ariëns, Maxim I. Matsuo, Bianca T. de Vries, Steven van Wordragen, Ellen D. H. Ellenbroek, Brecht D. Vande Velde, Christophe M. L. Orru, Romano V. A. Ruijter, Eelco Stereoselective Synthesis of Fused Vinylcyclopropanes by Intramolecular Tsuji–Trost Cascade Cyclization |
| title | Stereoselective Synthesis of Fused Vinylcyclopropanes
by Intramolecular Tsuji–Trost Cascade Cyclization |
| title_full | Stereoselective Synthesis of Fused Vinylcyclopropanes
by Intramolecular Tsuji–Trost Cascade Cyclization |
| title_fullStr | Stereoselective Synthesis of Fused Vinylcyclopropanes
by Intramolecular Tsuji–Trost Cascade Cyclization |
| title_full_unstemmed | Stereoselective Synthesis of Fused Vinylcyclopropanes
by Intramolecular Tsuji–Trost Cascade Cyclization |
| title_short | Stereoselective Synthesis of Fused Vinylcyclopropanes
by Intramolecular Tsuji–Trost Cascade Cyclization |
| title_sort | stereoselective synthesis of fused vinylcyclopropanes
by intramolecular tsuji–trost cascade cyclization |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6218879/ https://www.ncbi.nlm.nih.gov/pubmed/30350659 http://dx.doi.org/10.1021/acs.orglett.8b02232 |
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