Pure Appl. Chem., 2005, Vol. 77, No. 12, pp. 2091-2098
doi:10.1351/pac200577122091
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: (1-phosphoryl)vinyl sulfoxides; 2-amino-cyclopropanephosphonic acid; Asymmetric cyclopropanation; cyclopropylphosphonate analogs of nucleotides; sulfur ylides.