The Journal of organic chemistry

A three-component, one-pot synthesis of indolizidines and related heterocycles via the [3+ 2] cycloaddition of nonstabilized azomethine ylides

WH Pearson, P Stoy, Y Mi

Index: Pearson, William H.; Stoy, Patrick; Mi, Yuan Journal of Organic Chemistry, 2004 , vol. 69, # 6 p. 1919 - 1939

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Citation Number: 48

Abstract

Nonstabilized azomethine ylides (ie those bearing only hydrogens or alkyl groups) can be generated from (2-azaallyl) stannanes and (2-azaallyl) silanes through an intramolecular N- alkylation/demetalation cascade. The resulting ylides undergo [3+ 2] cycloaddition with electron-poor or electron-rich dipolarophiles yielding indolizidines and related 1-aza [m. 3.0] bicycloalkane systems in good yield. An in situ protocol allows for a one-pot, three- ...