Dimethylsulfonium Methylide: A Versatile Reagent

Introduction

Dimethylsulfonium methylide, Me₂SCH₂, was reported by Corey and Chaykovsky for the first time in 1962. [¹] It is a versatile nucleophile which can insert the methylene unit into certain unsaturated linkages, such as C=O and C=C, to form epoxides and cyclopropanes, respectively. [²] Utilization of this reagent is a reliable method in many synthetic applications and it has been well-utilized in the synthesis of functional molecules, especially bioactive natural products.

References

• 1 Corey EJ. Chaykovsky M. J. Am. Chem. Soc.  1962,  84:  3782 
• 2 Corey EJ. Chaykovsky M. J. Am. Chem. Soc.  1965,  87:  1353 
• 3 Cwynar V. Donahue MG. Hart DJ. Yang D. Org. Lett.  2006,  8:  4577 
• 4 Cleij M. Archelas A. Furstoss R. J. Org. Chem.  1999,  64:  5029 
• 5 Herscovici J. Uriel C. Uriel J. Antonakis K. Bioorg. Med. Chem. Lett.  1994,  4:  421 
• 6 Di Chenna P. Ghini AA. Burton G. Molecules  2000,  5:  447 
• 7 Morton D. Pearson D. Field RA. Stockman RA. Synlett  2003,  1985 
• 8 Raj IVP. Sudalai A. Tetrahedron Lett.  2008,  49:  2646 
• 9 Hodgson DM. Fleming MJ. Stanway SJ. Org. Lett.  2005,  7:  3295 
• 10 Benoit-Marquie F. Csákÿ AG. Esteban G. Martínez ME. Plumet J. Tetrahedron Lett.  2000,  41:  3355 
• 11 Singh R. Singh GC. Ghosh SK. Eur. J. Org. Chem.  2007,  5376 
• 12 Panda K. Venkatesh C. Ila H. Junjappa H. Eur. J. Org. Chem.  2005,  2045 
• 13 Kumar S. Ila H. Junjappa H. Tetrahedron  2007,  63:  10067 
• 14 Schinkels B. Ruban A. Nieger M. Niecke E. J. Chem. Soc., Chem. Commun.  1997,  293