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

doi:10.1021/jo016174w

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 language	English (US)
Pages (from-to)	2919-2925
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	67
Issue number	9
DOIs	https://doi.org/10.1021/jo016174w
State	Published - May 3 2002

ASJC Scopus subject areas

Organic Chemistry

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

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.",

author = "{Garc{\'i}a Ruano}, {Jos{\'e} L.} and Carlos Alemparte and Clemente, {Fernando R.} and {Gonz{\'a}lez Guti{\'e}rrez}, Lorena and Ruth Gordillo and {Mart{\'i}n Castro}, {Ana M.} and {Rodr{\'i}guez Ramos}, {Jes{\'u}s H.}",

year = "2002",

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doi = "10.1021/jo016174w",

language = "English (US)",

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journal = "Journal of Organic Chemistry",

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T1 - Cyclic vinyl p-tolyl sulfilimines as chiral dienophiles

T2 - Diels-Alder reactions with furan and acyclic dienes

AU - García Ruano, José L.

AU - Alemparte, Carlos

AU - Clemente, Fernando R.

AU - González Gutiérrez, Lorena

AU - Gordillo, Ruth

AU - Martín Castro, Ana M.

AU - Rodríguez Ramos, Jesús H.

PY - 2002/5/3

Y1 - 2002/5/3

N2 - 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.

AB - 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.

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

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