Tetrahedron

The effect of pre-existing stereocenters in the intramolecular asymmetric Stetter reaction

NT Reynolds, T Rovis

Index: Reynolds, Nathan T.; Rovis, Tomislav Tetrahedron, 2005 , vol. 61, # 26 p. 6368 - 6378

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Citation Number: 51

Abstract

A series of disubstituted cyclopentanones have been synthesized by the intramolecular Stetter reaction. Racemic substrates containing one chiral center were used, allowing us the opportunity to observe a parallel kinetic resolution in the synthesis of 2, 3-and 2, 4- disubstituted cyclopentanones. The Stetter reaction of 2, 5-disubstituted cyclopentanones proved to be substrate controlled, resulting in the selective formation of the cis- ...