Reaction of carbonyl compounds with ethyl lithiodiazoacetate. Studies dealing with the rhodium (II)-catalyzed behavior of the resulting adducts

A Padwa, YS Kulkarni, Z Zhang

Index: Padwa, Albert; Kulkarni, Yashwant S.; Zhang, Zhijia Journal of Organic Chemistry, 1990 , vol. 55, # 13 p. 4144 - 4153

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Citation Number: 110

Abstract

The carbenoid intermediate derived by treating ethyl 2-diazo-4-phthalimidobutyrate with rhodium (I1) octanoate undergoes transannular cyclization onto the adjacent imido carbonyl group. The resulting cyclic carbonyl ylide dipole was trapped with several dipolarophiles. In an attempt to prepare related substrates for cyclization studies, the reaction of ethyl lithiodiazoacetate with various aldehydes and ketones was studied. Treatment of the a- ...