Cyclic Vinyl p-Tolyl Sulfilimines as Chiral Dienophiles:  Diels−Alder Reactions with Furan and Acyclic Dienes

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 th...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-05, Vol.67 (9), p.2919-2925
Main Authors: García Ruano, José L, Alemparte, Carlos, Clemente, Fernando R, González Gutiérrez, Lorena, Gordillo, Ruth, Martín Castro, Ana M, Rodríguez Ramos, Jesús H
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Preparations and properties
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo016174w