Asymmetric cyclopropanation of chiral (1-phosphoryl)vinyl sulfoxides: A new approach to constrained analogs of biologically active compounds*
Marian Mikolajczyk
Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90-363 Łódź, Sienkiewicza 112, Poland
Abstract: This account outlines the results obtained in the author's laboratory on the asymmetric cyclopropanation of enantiopure 1-phosphorylvinyl p-tolyl sulfoxides with sulfur ylides and diazoalkanes. Based on experimental results and theoretical calculations, the transition-state model for asymmetric cyclopropanation is proposed. A great synthetic value of the reaction investigated is exemplified by the total synthesis of constrained analogs of bioactive compounds, namely, enantiopure cyclic analog of phaclofen and cyclopropylphosphonate analogs of nucleotides.
Keywords: Asymmetric cyclopropanation; (1-phosphoryl)vinyl sulfoxides; 2-amino-cyclopropanephosphonic acid; cyclopropylphosphonate analogs of nucleotides; sulfur ylides.
*Paper based on a presentation at the 7th IUPAC International Conference on Heteroatom Chemistry (ICHAC-7), Shanghai, China, 21-25 August 2004. Other presentations are published in this issue, pp. 1985-2132.