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Synthesis 1995; 1995(4): 347-360
DOI: 10.1055/s-1995-3934
review
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Imino Ene Reactions in Organic Synthesis

Robert M. Borzilleri, Steven M. Weinreb*
  • *Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA, Fax +1(814)8638403
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Publikationsdatum:
31. Dezember 2000 (online)

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During the last decade the ene reaction has achieved wide recognition as a powerful carbon-carbon bond forming method in synthetic organic chemistry. The imino ene reaction, however, is still a relatively rare transformation despite its potential for preparation of nitrogen heterocycles and in alkaloid total synthesis. This review describes mechanistic aspects of the imino ene reaction and illustrates a number of synthetic application of this versatile process. The details of inter- and intramolecular imino ene reactions involving N-alkyl, N-acyl, and N-sulfonyl imines or iminium ions are presented with particular emphasis on the regio- and stereochemical issues accompanying these processes. A discussion of retro imino ene reactions is also included.

retro ene reactions - pericyclic reactions - cycloadditions - imines