Synthesis 2017; 49(12): 2652-2662
DOI: 10.1055/s-0036-1588971
paper
© Georg Thieme Verlag Stuttgart · New York

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

Edward T. Ledingham
a   School of Science and Technology, University of New England, Armidale, New South Wales, 2351, Australia   Email: ben.greatrex@une.edu.au
,
Christopher J. Merritt
a   School of Science and Technology, University of New England, Armidale, New South Wales, 2351, Australia   Email: ben.greatrex@une.edu.au
,
Christopher J. Sumby
b   Department of Chemistry, School of Physical Sciences, The University of Adelaide, Adelaide, South Australia, 5005, Australia
,
Michelle K. Taylor
a   School of Science and Technology, University of New England, Armidale, New South Wales, 2351, Australia   Email: ben.greatrex@une.edu.au
,
Ben W. Greatrex*
a   School of Science and Technology, University of New England, Armidale, New South Wales, 2351, Australia   Email: ben.greatrex@une.edu.au
› Author Affiliations
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

 
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