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Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition
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| Zeitschriftentitel: | Angewandte Chemie International Edition |
|---|---|
| Personen und Körperschaften: | , |
| In: | Angewandte Chemie International Edition, 55, 2016, 23, S. 6780-6783 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Wiley
|
| Schlagwörter: |
| author_facet |
Sabbatani, Juliette Maulide, Nuno Sabbatani, Juliette Maulide, Nuno |
|---|---|
| author |
Sabbatani, Juliette Maulide, Nuno |
| spellingShingle |
Sabbatani, Juliette Maulide, Nuno Angewandte Chemie International Edition Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition General Chemistry Catalysis |
| author_sort |
sabbatani, juliette |
| spelling |
Sabbatani, Juliette Maulide, Nuno 1433-7851 1521-3773 Wiley General Chemistry Catalysis http://dx.doi.org/10.1002/anie.201601340 <jats:title>Abstract</jats:title><jats:p>A novel formal [3+2] cycloaddition of cyclopropylacetals and aldehydes was developed, and the resulting trisubstituted tetrahydrofurans display three new chiral centers formed with highly diastereoselectivity. This method is stereocomplementary to most previously reported cycloadditions of malonate diesters, relies on the transient generation of cyclopropyl oxocarbenium ions, proceeds under mild conditions, and is based on the concept of temporary activation of an otherwise inert protecting group.</jats:p> Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition Angewandte Chemie International Edition |
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| title |
Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition |
| title_unstemmed |
Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition |
| title_full |
Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition |
| title_fullStr |
Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition |
| title_full_unstemmed |
Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition |
| title_short |
Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition |
| title_sort |
temporary generation of a cyclopropyl oxocarbenium ion enables highly diastereoselective donor–acceptor cyclopropane cycloaddition |
| topic |
General Chemistry Catalysis |
| url |
http://dx.doi.org/10.1002/anie.201601340 |
| publishDate |
2016 |
| physical |
6780-6783 |
| description |
<jats:title>Abstract</jats:title><jats:p>A novel formal [3+2] cycloaddition of cyclopropylacetals and aldehydes was developed, and the resulting trisubstituted tetrahydrofurans display three new chiral centers formed with highly diastereoselectivity. This method is stereocomplementary to most previously reported cycloadditions of malonate diesters, relies on the transient generation of cyclopropyl oxocarbenium ions, proceeds under mild conditions, and is based on the concept of temporary activation of an otherwise inert protecting group.</jats:p> |
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| author | Sabbatani, Juliette, Maulide, Nuno |
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| description | <jats:title>Abstract</jats:title><jats:p>A novel formal [3+2] cycloaddition of cyclopropylacetals and aldehydes was developed, and the resulting trisubstituted tetrahydrofurans display three new chiral centers formed with highly diastereoselectivity. This method is stereocomplementary to most previously reported cycloadditions of malonate diesters, relies on the transient generation of cyclopropyl oxocarbenium ions, proceeds under mild conditions, and is based on the concept of temporary activation of an otherwise inert protecting group.</jats:p> |
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| imprint | Wiley, 2016 |
| imprint_str_mv | Wiley, 2016 |
| institution | DE-Ch1, DE-L229, DE-D275, DE-Bn3, DE-Brt1, DE-D161, DE-Gla1, DE-Zi4, DE-15, DE-Pl11, DE-Rs1, DE-105, DE-14 |
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| physical | 6780-6783 |
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| series | Angewandte Chemie International Edition |
| source_id | 49 |
| spelling | Sabbatani, Juliette Maulide, Nuno 1433-7851 1521-3773 Wiley General Chemistry Catalysis http://dx.doi.org/10.1002/anie.201601340 <jats:title>Abstract</jats:title><jats:p>A novel formal [3+2] cycloaddition of cyclopropylacetals and aldehydes was developed, and the resulting trisubstituted tetrahydrofurans display three new chiral centers formed with highly diastereoselectivity. This method is stereocomplementary to most previously reported cycloadditions of malonate diesters, relies on the transient generation of cyclopropyl oxocarbenium ions, proceeds under mild conditions, and is based on the concept of temporary activation of an otherwise inert protecting group.</jats:p> Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition Angewandte Chemie International Edition |
| spellingShingle | Sabbatani, Juliette, Maulide, Nuno, Angewandte Chemie International Edition, Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition, General Chemistry, Catalysis |
| title | Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition |
| title_full | Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition |
| title_fullStr | Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition |
| title_full_unstemmed | Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition |
| title_short | Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition |
| title_sort | temporary generation of a cyclopropyl oxocarbenium ion enables highly diastereoselective donor–acceptor cyclopropane cycloaddition |
| title_unstemmed | Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor–Acceptor Cyclopropane Cycloaddition |
| topic | General Chemistry, Catalysis |
| url | http://dx.doi.org/10.1002/anie.201601340 |