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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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

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Butadienes
Regioselectivity
Cycloaddition
furan
sulfilimine

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

Cyclic vinyl p-tolyl sulfilimines as chiral dienophiles : Diels-Alder reactions with furan and acyclic dienes. / García Ruano, José L.; Alemparte, Carlos; Clemente, Fernando R.; González Gutiérrez, Lorena; Gordillo, Ruth; Martín Castro, Ana M.; Rodríguez Ramos, Jesús H.

In: Journal of Organic Chemistry, Vol. 67, No. 9, 03.05.2002, p. 2919-2925.

Research output: Contribution to journalArticle

García Ruano, JL, Alemparte, C, Clemente, FR, González Gutiérrez, L, Gordillo, R, Martín Castro, AM & Rodríguez Ramos, JH 2002, 'Cyclic vinyl p-tolyl sulfilimines as chiral dienophiles: Diels-Alder reactions with furan and acyclic dienes', Journal of Organic Chemistry, vol. 67, no. 9, pp. 2919-2925. https://doi.org/10.1021/jo016174w
García Ruano JL, Alemparte C, Clemente FR, González Gutiérrez L, Gordillo R, Martín Castro AM et al. Cyclic vinyl p-tolyl sulfilimines as chiral dienophiles: Diels-Alder reactions with furan and acyclic dienes. Journal of Organic Chemistry. 2002 May 3;67(9):2919-2925. https://doi.org/10.1021/jo016174w
García Ruano, José L. ; Alemparte, Carlos ; Clemente, Fernando R. ; González Gutiérrez, Lorena ; Gordillo, Ruth ; Martín Castro, Ana M. ; Rodríguez Ramos, Jesús H. / Cyclic vinyl p-tolyl sulfilimines as chiral dienophiles : Diels-Alder reactions with furan and acyclic dienes. In: Journal of Organic Chemistry. 2002 ; Vol. 67, No. 9. pp. 2919-2925.
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