Cyclic vinyl p-tolyl sulfilimines as chiral dienophiles: Diels-Alder reactions with furan and acyclic dienes

José L. García Ruano, Carlos Alemparte, Fernando R. Clemente, Lorena González Gutiérrez, Ruth Gordillo, Ana M. Martín Castro, Jesús H. Rodríguez Ramos

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18 Scopus citations

Abstract

The dienophilic behavior of the sulfilimine 2, synthesized from (Z)-3-p-tolylsulfinylacrylonitrile 1, in its Diels-Alder reactions with furan and acyclic dienes has been investigated. A complete π-facial selectivity for 2, opposite to that observed from its precursor 1, is the main feature of all these cycloadditions. Moreover, the high exo selectivity observed in reactions of 2 with furan (not observed for 1) contrasts with the almost complete endo selectivity with other cyclic and acyclic dienes. Additionally, the opposite regioselectivities obtained for 2 with Dane's diene and 1-substituted butadienes (not observed for 1) are also noteworthy. This behavior allows dienophiles 1 and 2 to be considered as complementary precursors from a synthetic point of view.

Original languageEnglish (US)
Pages (from-to)2919-2925
Number of pages7
JournalJournal of Organic Chemistry
Volume67
Issue number9
DOIs
StatePublished - May 3 2002

ASJC Scopus subject areas

  • Organic Chemistry

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    García Ruano, J. L., Alemparte, C., Clemente, F. R., González Gutiérrez, L., Gordillo, R., Martín Castro, A. M., & Rodríguez Ramos, J. H. (2002). Cyclic vinyl p-tolyl sulfilimines as chiral dienophiles: Diels-Alder reactions with furan and acyclic dienes. Journal of Organic Chemistry, 67(9), 2919-2925. https://doi.org/10.1021/jo016174w