Une synthèse hautement stéréosélective de diènes conjugués (E)

1984 ◽  
Vol 62 (10) ◽  
pp. 2019-2024 ◽  
Author(s):  
R. Bloch ◽  
J. Abecassis ◽  
D. Hassan
Keyword(s):  
Sex Pheromone ◽  
Alder Reaction ◽  
Conjugated Dienes ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
General Method

A general method for the preparation of (E) terminal conjugated dienes was developed by the flash thermolysis of 2-substituted 2,5-dihydrothiophene-1,1-dioxides generated by a retro Diels–Alder reaction. This process allows the obtention of conjugated dienes, bearing or not a functionality (alcohols, esters), with an excellent stereoisomeric purity (in general higher than 98%). An application to the synthesis of (E)-9,11-dodecadien-1-yl acetate, the major component of the sex pheromone of Diparopsiscastanea, shows the generality and the efficacy of this method.

The synthesis of trisubstituted cyclopentadienes and their reactivity in the intramolecular Diels–Alder reaction

1984 ◽  
Vol 62 (1) ◽  
pp. 121-127 ◽  
Author(s):  
Sandra J. Alward ◽  
Alex G. Fallis
Keyword(s):  
Adverse Effect ◽  
Alder Reaction ◽  
Diels Alder ◽  
Keto Ester ◽  
Diels Alder Reaction ◽  
General Method

The intramolecular Diels–Alder reactivity of several trisubstituted cyclopentadienes is described and a general method for their preparation reported. In general, sidechain keto-ester functionality has an adverse effect on these internal cycloadditions.

Dihydrothiophenes.10. The preparation and Diels–Alder reactions of some sulfur and phosphorus-substituted dienophiles and 2-aza-substituted 1,3-dienes

1984 ◽  
Vol 62 (11) ◽  
pp. 2089-2093 ◽  
Author(s):  
John M. McIntosh ◽  
Lilianna Z. Pillon
Keyword(s):  
Thermal Decomposition ◽  
Alder Reaction ◽  
Conjugated Dienes ◽  
Diels Alder ◽  
Diels Alder Reaction

The use of 3-carboxylated 2,5-dihydrothiophenes as the dienophilic component of the Diels–Alder reaction has been investigated. The yields are generally quite low. The formation of conjugated dienes that are aminated at an interior position of the conjugated chain by formation and thermal decomposition of 3-acetamido-2,5-dihydrothiophenes appears to be a viable route to these useful compounds. One example of the Diels–Alder reaction of 2-carboxylated diethyl vinylphosphonates is reported.

Diels-Alder Reaction of Ni(II) β-Vinyl-meso-tetraphenylporphyrin; A General Method for Synthesis of Functionalized Porphyrins

Synlett ◽  
2000 ◽  
Vol 2000 (2) ◽  
pp. 233-235 ◽  
Author(s):  
Kiyoshi Matsumoto ◽  
Shinya Kimura ◽  
Takuya Morishita ◽  
Yukihiro Misumi ◽  
Naoto Hayashi
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
General Method

scholarly journals Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes

2016 ◽  
Vol 12 ◽  
pp. 1949-1980 ◽  
Author(s):  
Lucie Brulíková ◽  
Aidan Harrison ◽  
Marvin J Miller ◽  
Jan Hlaváč
Keyword(s):  
Alder Reaction ◽  
Conjugated Dienes ◽  
Diels Alder ◽  
Conjugated Diene ◽  
Diels Alder Reaction ◽  
Oxazine Ring

The hetero-Diels–Alder reaction between a nitroso dienophile and a conjugated diene to give the 3,6-dihydro-2H-1,2-oxazine scaffold is useful for the synthesis of many biologically interesting molecules due to the diverse opportunities created by subsequent transformations of the resulting 1,2-oxazine ring. This review discusses the rationale for the observed regio- and stereoselectivity and the methods developed in recent years used to control and improve the stereo- and regioselectivity for the synthesis of 1,2-oxazine scaffolds.

ChemInform Abstract: Diels-Alder Reaction of Ni(II) β-Vinyl-meso-tetraphenylporphyrin: A General Method for Synthesis of Functionalized Porphyrins.

ChemInform ◽  
2010 ◽  
Vol 31 (20) ◽  
pp. no-no
Author(s):  
Kiyoshi Matsumoto ◽  
Shinya Kimura ◽  
Takuya Morishita ◽  
Yukihiro Misumi ◽  
Naoto Hayashi
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
General Method
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