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https://hdl.handle.net/1959.11/21450
Title: | Stereoselective Cyclopropanation of (-)-Levoglucosenone Derivatives Using Sulfonium and Sulfoxonium Ylides | Contributor(s): | Ledingham, Edward (author); Merritt, Christopher J (author); Sumby, Christopher J (author); Taylor, Michelle K (author)![]() ![]() |
Publication Date: | 2017 | DOI: | 10.1055/s-0036-1588971 | Handle Link: | https://hdl.handle.net/1959.11/21450 | Abstract: | The synthesis of tri- and tetrasubstituted cyclopropanes from 3-aryl-substituted levoglucosenones (LGO) has been developed. In contrast to the unstabilised ylide dimethylsulfonium methylide which gives epoxides from LGO via 1,2-addition, we have found that the soft nucleophile dimethylsulfoxonium methylide affords cyclopropanes in moderate yields from LGO and in excellent yields and stereoselectivity with 3-aryl LGO derivatives. The use of 1,1,3,3-tetramethylguanidine as base in DMSO to generate the ylide provided the best yields and shortest reaction times. Ester stabilised sulfonium ylides could also be used to generate tetrasubstituted cyclopropane derivatives. One of the products was converted into a cyclopropyl lactone via Baeyer-Villiger oxidation to demonstrate the utility of applying cyclopropanation chemistry to LGO. | Publication Type: | Journal Article | Source of Publication: | Synthesis, 49(12), p. 2652-2662 | Publisher: | Georg Thieme Verlag | Place of Publication: | Germany | ISSN: | 1437-210X 0039-7881 |
Fields of Research (FoR) 2008: | 030504 Organic Green Chemistry 030503 Organic Chemical Synthesis 030401 Biologically Active Molecules |
Fields of Research (FoR) 2020: | 340504 Organic green chemistry 340503 Organic chemical synthesis 340401 Biologically active molecules |
Socio-Economic Objective (SEO) 2008: | 970103 Expanding Knowledge in the Chemical Sciences | Socio-Economic Objective (SEO) 2020: | 280105 Expanding knowledge in the chemical sciences | Peer Reviewed: | Yes | HERDC Category Description: | C1 Refereed Article in a Scholarly Journal |
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Appears in Collections: | Journal Article |
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