Electronic and steric control in carbon-hydrogen insertion reactions of diazoacetoacetates catalyzed by dirhodium (II) carboxylates and carboxamides

MP Doyle, LJ Westrum, WNE Wolthuis…

Index: Doyle, Michael P.; Westrum, Larry J.; Wolthuis, Wendelmoed N. E.; See, Marjorie M.; Boone, William P.; Bagheri, Vahid; Pearson, Matthew M. Journal of the American Chemical Society, 1993 , vol. 115, # 3 p. 958 - 964

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Citation Number: 264

Abstract

Abstract: Carboxylate and carboxamide ligands on dirhodium (I1) catalysts can provide enormous regiocontrol in carbon-hydrogen insertion reactions of diazoasetate esters. Whereas 2, 3, 4-trimethyl-3-pentyl diazoacetoacetate (1) forms y-lactone products from insertion into primary and tertiary CH bonds in a statistical distribution (61: 39) with dirhodium (I1) tetrakis (perfluorobutyrate), only tertiary CH insertion is observed with ...