Stereoselective Cyclopropanation of (-)-Levoglucosenone Derivatives Using Sulfonium and Sulfoxonium Ylides

Title
Stereoselective Cyclopropanation of (-)-Levoglucosenone Derivatives Using Sulfonium and Sulfoxonium Ylides
Publication Date
2017
Author(s)
Ledingham, Edward
Merritt, Christopher J
Sumby, Christopher J
Taylor, Michelle K
( author )
OrcID: https://orcid.org/0000-0002-0280-8359
Email: mtaylo53@une.edu.au
UNE Id une-id:mtaylo53
Greatrex, Ben
( author )
OrcID: https://orcid.org/0000-0002-0356-4966
Email: bgreatre@une.edu.au
UNE Id une-id:bgreatre
Type of document
Journal Article
Language
en
Entity Type
Publication
Publisher
Georg Thieme Verlag
Place of publication
Germany
DOI
10.1055/s-0036-1588971
UNE publication id
une:21642
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.
Link
Citation
Synthesis, 49(12), p. 2652-2662
ISSN
1437-210X
0039-7881
Start page
2652
End page
2662

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