Utility of a chiral 1,3-dioxane template in stereoselective intramolecular Diels-Alder reactions

Laurent Evanno; Alexandre Deville; Lionel Dubost; Angèle Chiaroni; Bernard Bodo; Bastien Nay

doi:10.1016/j.tetlet.2007.02.089

Utility of a chiral 1,3-dioxane template in stereoselective intramolecular Diels-Alder reactions

Laurent Evanno
, Alexandre Deville
, Lionel Dubost
, Angèle Chiaroni
, Bernard Bodo
, Bastien Nay

CNRS/Museum National d'Histoire Naturelle/IRD/UPMC
CNRS

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

Résumé

The ethylidene acetal of d-erythrose was used as a template for stereoselective IMDA reactions: high endo selectivity and yields in favor of the cis product were observed with 1,3,9-trienes, resulting from a boat transition state. For natural product synthesis, the reaction was successfully applied to a diene with terminal Z-olefin.

langue originale	Anglais
Pages (de - à)	2893-2896
Nombre de pages	4
journal	Tetrahedron Letters
Volume	48
Numéro de publication	16
Les DOIs	https://doi.org/10.1016/j.tetlet.2007.02.089
état	Publié - 16 avr. 2007
Modification externe	Oui

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10.1016/j.tetlet.2007.02.089

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title = "Utility of a chiral 1,3-dioxane template in stereoselective intramolecular Diels-Alder reactions",

abstract = "The ethylidene acetal of d-erythrose was used as a template for stereoselective IMDA reactions: high endo selectivity and yields in favor of the cis product were observed with 1,3,9-trienes, resulting from a boat transition state. For natural product synthesis, the reaction was successfully applied to a diene with terminal Z-olefin.",

keywords = "Diels-Alder reaction, Stereoselectivity, Total synthesis, Z-Diene, endo-Boat transition state",

author = "Laurent Evanno and Alexandre Deville and Lionel Dubost and Ang{\`e}le Chiaroni and Bernard Bodo and Bastien Nay",

year = "2007",

month = apr,

day = "16",

doi = "10.1016/j.tetlet.2007.02.089",

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journal = "Tetrahedron Letters",

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T1 - Utility of a chiral 1,3-dioxane template in stereoselective intramolecular Diels-Alder reactions

AU - Evanno, Laurent

AU - Deville, Alexandre

AU - Dubost, Lionel

AU - Chiaroni, Angèle

AU - Bodo, Bernard

AU - Nay, Bastien

PY - 2007/4/16

Y1 - 2007/4/16

N2 - The ethylidene acetal of d-erythrose was used as a template for stereoselective IMDA reactions: high endo selectivity and yields in favor of the cis product were observed with 1,3,9-trienes, resulting from a boat transition state. For natural product synthesis, the reaction was successfully applied to a diene with terminal Z-olefin.

AB - The ethylidene acetal of d-erythrose was used as a template for stereoselective IMDA reactions: high endo selectivity and yields in favor of the cis product were observed with 1,3,9-trienes, resulting from a boat transition state. For natural product synthesis, the reaction was successfully applied to a diene with terminal Z-olefin.

KW - Diels-Alder reaction

KW - Stereoselectivity

KW - Total synthesis

KW - Z-Diene

KW - endo-Boat transition state

UR - https://www.scopus.com/pages/publications/33947206554

U2 - 10.1016/j.tetlet.2007.02.089

DO - 10.1016/j.tetlet.2007.02.089

M3 - Article

AN - SCOPUS:33947206554

SN - 0040-4039

VL - 48

SP - 2893

EP - 2896

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 16

ER -

Utility of a chiral 1,3-dioxane template in stereoselective intramolecular Diels-Alder reactions

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