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Pure Appl. Chem., 2005, Vol. 77, No. 12, pp. 2091-2098

Asymmetric cyclopropanation of chiral (1-phosphoryl)vinyl sulfoxides: A new approach to constrained analogs of biologically active compounds

Marian Mikołajczyk

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.