Intramolecular regioselective insertion into unactivated prochiral carbon-hydrogen bonds with diazoacetates of primary alcohols catalyzed by chiral dirhodium (II) …

JW Bode, MP Doyle, MN Protopopova…

Index: Bode; Doyle; Protopopova; Zhou Journal of Organic Chemistry, 1996 , vol. 61, # 26 p. 9146 - 9155

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Citation Number: 145

Abstract

Intramolecular insertion into unactivated prochiral CH bonds of 3-aryl-1-propyl diazoacetates catalyzed by dirhodium (II) tetrakis [methyl 1-(3-phenyl propanoyl) imidazolidin-2-one-4 (R or S)-carboxylate], Rh2 (4 R-MPPIM) 4 or Rh2 (4 S-MPPIM) 4, occurs in 91-96% ee and with virtually complete regiocontrol for the formation of β-benzyl-γ- butyrolactones. This methodology has been applied to the total synthesis of ...