Recent Developments in Stereoselective Reactions of Sulfonium Ylides
This review describes advances in the literature since the mid-1990s in the area of reactions of sulfonium ylide chemistry, with particular attention paid to stereoselective examples. Although the chemistry of sulfonium ylides was first popularized and applied in a substantial way in the 1960s, ther...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-09-01
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| Series: | Organics |
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| Online Access: | https://www.mdpi.com/2673-401X/3/3/24 |
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| author | Mukulesh Mondal Sophie Connolly Shi Chen Shubhanjan Mitra Nessan J. Kerrigan |
| author_facet | Mukulesh Mondal Sophie Connolly Shi Chen Shubhanjan Mitra Nessan J. Kerrigan |
| author_sort | Mukulesh Mondal |
| collection | DOAJ |
| description | This review describes advances in the literature since the mid-1990s in the area of reactions of sulfonium ylide chemistry, with particular attention paid to stereoselective examples. Although the chemistry of sulfonium ylides was first popularized and applied in a substantial way in the 1960s, there has been sustained interest in the chemistry of sulfonium ylides since then. Many new ways of exploiting sulfonium ylides in productive stereoselective methodologies have emerged, often taking advantage of advances in organocatalysis and transition metal catalysis, to access stereodefined structurally complex motifs. The development of many different chiral sulfides over the last 20–30 years has also played a role in accelerating their study in a variety of reaction settings. In general, formal cycloaddition reactions ([2 + 1] and [4 + 1]) of sulfonium ylides follow a similar mechanistic pathway: initial addition of the nucleophilic ylide carbanion to an electrophile to form a zwitterionic betaine intermediate, followed by cyclization of the zwitterionic intermediate to afford the desired three-membered cyclic product (e.g., epoxide, cyclopropane, or aziridine), five-membered monocyclic (e.g., oxazolidinone), or fused bicyclic product (e.g., benzofuran, indoline). |
| first_indexed | 2024-03-09T22:53:56Z |
| format | Article |
| id | doaj.art-23ee63cefc6c48048edb43e1438efbde |
| institution | Directory Open Access Journal |
| issn | 2673-401X |
| language | English |
| last_indexed | 2024-03-09T22:53:56Z |
| publishDate | 2022-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Organics |
| spelling | doaj.art-23ee63cefc6c48048edb43e1438efbde2023-11-23T18:14:40ZengMDPI AGOrganics2673-401X2022-09-013332036310.3390/org3030024Recent Developments in Stereoselective Reactions of Sulfonium YlidesMukulesh Mondal0Sophie Connolly1Shi Chen2Shubhanjan Mitra3Nessan J. Kerrigan4Department of Chemistry, Oakland University, Rochester, MI 40309, USASchool of Chemical Sciences, Dublin City University, Glasnevin, D09 V209 Dublin, IrelandDepartment of Chemistry, Oakland University, Rochester, MI 40309, USASchool of Chemical Sciences, Dublin City University, Glasnevin, D09 V209 Dublin, IrelandSchool of Chemical Sciences, Dublin City University, Glasnevin, D09 V209 Dublin, IrelandThis review describes advances in the literature since the mid-1990s in the area of reactions of sulfonium ylide chemistry, with particular attention paid to stereoselective examples. Although the chemistry of sulfonium ylides was first popularized and applied in a substantial way in the 1960s, there has been sustained interest in the chemistry of sulfonium ylides since then. Many new ways of exploiting sulfonium ylides in productive stereoselective methodologies have emerged, often taking advantage of advances in organocatalysis and transition metal catalysis, to access stereodefined structurally complex motifs. The development of many different chiral sulfides over the last 20–30 years has also played a role in accelerating their study in a variety of reaction settings. In general, formal cycloaddition reactions ([2 + 1] and [4 + 1]) of sulfonium ylides follow a similar mechanistic pathway: initial addition of the nucleophilic ylide carbanion to an electrophile to form a zwitterionic betaine intermediate, followed by cyclization of the zwitterionic intermediate to afford the desired three-membered cyclic product (e.g., epoxide, cyclopropane, or aziridine), five-membered monocyclic (e.g., oxazolidinone), or fused bicyclic product (e.g., benzofuran, indoline).https://www.mdpi.com/2673-401X/3/3/24sulfoniumylidesconjugate additionepoxidecyclopropaneaziridine |
| spellingShingle | Mukulesh Mondal Sophie Connolly Shi Chen Shubhanjan Mitra Nessan J. Kerrigan Recent Developments in Stereoselective Reactions of Sulfonium Ylides Organics sulfonium ylides conjugate addition epoxide cyclopropane aziridine |
| title | Recent Developments in Stereoselective Reactions of Sulfonium Ylides |
| title_full | Recent Developments in Stereoselective Reactions of Sulfonium Ylides |
| title_fullStr | Recent Developments in Stereoselective Reactions of Sulfonium Ylides |
| title_full_unstemmed | Recent Developments in Stereoselective Reactions of Sulfonium Ylides |
| title_short | Recent Developments in Stereoselective Reactions of Sulfonium Ylides |
| title_sort | recent developments in stereoselective reactions of sulfonium ylides |
| topic | sulfonium ylides conjugate addition epoxide cyclopropane aziridine |
| url | https://www.mdpi.com/2673-401X/3/3/24 |
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