Please use this identifier to cite or link to this item: 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); Greatrex, Ben (author)orcid 
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
Field of Research (FOR): 030504 Organic Green Chemistry
030503 Organic Chemical Synthesis
030401 Biologically Active Molecules
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
Statistics to Oct 2018: Visitors: 19
Views: 222
Downloads: 0
Appears in Collections:Journal Article

Files in This Item:
3 files
File Description SizeFormat 
Show full item record

SCOPUSTM   
Citations

7
checked on Nov 26, 2018

Page view(s)

42
checked on Mar 21, 2019
Google Media

Google ScholarTM

Check

Altmetric

SCOPUSTM   
Citations

 

WEB OF SCIENCETM
Citations

 

Items in Research UNE are protected by copyright, with all rights reserved, unless otherwise indicated.