Synthesis of Functionalized Azomethine Ylides via the Rh (II)-Catalyzed Cyclization of. alpha.-Diazo Carbonyls onto Imino. pi.-Bonds

…, MH Osterhout, L Precedo, MA Semones

Index: Padwa, Albert; Dean, Dennis C.; Osterhout, Martin H.; Precedo, Laura; Semones, Mark A. Journal of Organic Chemistry, 1994 , vol. 59, # 18 p. 5347 - 5357

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Citation Number: 52

Abstract

a-Diazo carbonyl compounds containing an imino group in the y-position have been found to undergo a rhodium (I1) acetate induced cyclization reaction to generate cyclic azomethine ylides. The reactive dipole undergoes a subsequent 1, 3-dipolar cycloaddition with added dipolarophiles. The imino/oxime nitrogen lone pair of electrons must be properly oriented so as to interact with the rhodium carbenoid. Thus, acyclic oxime ethers which exist in the ...