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

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	2893-2896
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	16
DOIs	https://doi.org/10.1016/j.tetlet.2007.02.089
Publication status	Published - 16 Apr 2007
Externally published	Yes

Keywords

Diels-Alder reaction
Stereoselectivity
Total synthesis
Z-Diene
endo-Boat transition state

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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",

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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

Abstract

Keywords

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