One-pot synthesis of epoxides from benzyl alcohols and aldehydes
A one-pot synthesis of epoxides from commercially available benzyl alcohols and aldehydes is described. The reaction proceeds through in situ generation of sulfonium salts from benzyl alcohols and their subsequent deprotonation for use in Corey–Chaykovsky epoxidation of aldehydes. The generality of...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2018-09-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.14.205 |
| _version_ | 1818368176706027520 |
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| author | Edwin Alfonzo Jesse W. L. Mendoza Aaron B. Beeler |
| author_facet | Edwin Alfonzo Jesse W. L. Mendoza Aaron B. Beeler |
| author_sort | Edwin Alfonzo |
| collection | DOAJ |
| description | A one-pot synthesis of epoxides from commercially available benzyl alcohols and aldehydes is described. The reaction proceeds through in situ generation of sulfonium salts from benzyl alcohols and their subsequent deprotonation for use in Corey–Chaykovsky epoxidation of aldehydes. The generality of the method is exemplified by the synthesis of 34 epoxides that were made from an array of electronically and sterically varied alcohols and aldehydes. |
| first_indexed | 2024-12-13T23:03:47Z |
| format | Article |
| id | doaj.art-5701f8d28650459db9cc01c179b09005 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-13T23:03:47Z |
| publishDate | 2018-09-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-5701f8d28650459db9cc01c179b090052022-12-21T23:28:20ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-09-011412308231210.3762/bjoc.14.2051860-5397-14-205One-pot synthesis of epoxides from benzyl alcohols and aldehydesEdwin Alfonzo0Jesse W. L. Mendoza1Aaron B. Beeler2Department of Chemistry, Boston University, Boston, Massachusetts 02215, United StatesDepartment of Chemistry, Boston University, Boston, Massachusetts 02215, United StatesDepartment of Chemistry, Boston University, Boston, Massachusetts 02215, United StatesA one-pot synthesis of epoxides from commercially available benzyl alcohols and aldehydes is described. The reaction proceeds through in situ generation of sulfonium salts from benzyl alcohols and their subsequent deprotonation for use in Corey–Chaykovsky epoxidation of aldehydes. The generality of the method is exemplified by the synthesis of 34 epoxides that were made from an array of electronically and sterically varied alcohols and aldehydes.https://doi.org/10.3762/bjoc.14.205Corey–Chaykovskyepoxideheterocycleone-potylide |
| spellingShingle | Edwin Alfonzo Jesse W. L. Mendoza Aaron B. Beeler One-pot synthesis of epoxides from benzyl alcohols and aldehydes Beilstein Journal of Organic Chemistry Corey–Chaykovsky epoxide heterocycle one-pot ylide |
| title | One-pot synthesis of epoxides from benzyl alcohols and aldehydes |
| title_full | One-pot synthesis of epoxides from benzyl alcohols and aldehydes |
| title_fullStr | One-pot synthesis of epoxides from benzyl alcohols and aldehydes |
| title_full_unstemmed | One-pot synthesis of epoxides from benzyl alcohols and aldehydes |
| title_short | One-pot synthesis of epoxides from benzyl alcohols and aldehydes |
| title_sort | one pot synthesis of epoxides from benzyl alcohols and aldehydes |
| topic | Corey–Chaykovsky epoxide heterocycle one-pot ylide |
| url | https://doi.org/10.3762/bjoc.14.205 |
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