Vinyl sulfoxides as stereochemical controllers in intermolecular Pauson–Khand reactions: Applications to the enantioselective synthesis of natural cyclopentanoids

M Rodríguez Rivero, I Alonso…

Index: Rodriguez Rivero, Marta; Alonso, Ines; Carretero, Juan C. Chemistry - A European Journal, 2004 , vol. 10, # 21 p. 5443 - 5459

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Citation Number: 41

Abstract

Abstract The use of sulfoxides as chiral auxiliaries in asymmetric intermolecular Pauson– Khand reactions is described. After screening a wide variety of substituents on the sulfur atom in α, β-unsaturated sulfoxides, the readily available o-(N, N-dimethylamino) phenyl vinyl sulfoxide (1 i) has proved to be highly reactive with substituted terminal alkynes under N-oxide-promoted conditions (CH 3 CN, 0 C). In addition, these Pauson–Khand reactions ...