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Synthesis 2017; 49(12): 2652-2662
DOI: 10.1055/s-0036-1588971
DOI: 10.1055/s-0036-1588971
paper
Stereoselective Cyclopropanation of (–)-Levoglucosenone Derivatives Using Sulfonium and Sulfoxonium Ylides
Further Information
Publication History
Received: 26 January 2017
Accepted after revision: 20 February 2017
Publication Date:
17 March 2017 (online)
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.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588971.
- Supporting Information
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For reviews on the chemistry of LGO see:
For recent synthetic applications see: