Asymmetric Diels-Alder reaction of 1,3-butadienes with (−)-dimenthyl fumarate in the presence of BBr3 and BBr3·OEt2

Mamedov, E. G.

doi:10.1134/s1070428007020054

Cited by 4 publications

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“…in 1963 in the same AlCl 3 mediated cycloaddition . (For ulterior [4+2] cycloadditions to buta‐1,3‐diene 3 a . For specific high pressure conditions ,.…”

Section: Introductionmentioning

confidence: 99%

“…For specific high pressure conditions ,. For cycloadditions of bis ‐menthyl fumarate to other non‐cyclic dienes,,,), as well as by Sauer and Kredel with cyclopenta‐1,3‐diene 3 b , (For further cycloadditions to cyclic dienes,,), while a sterically much more bulky 8‐Phenyl‐menthol analogue (‐)‐ 1 d was later designed, for a similar acrylate [4+2] cycloaddition, by Corey and Ensley , then others . Oppolzer et al .…”

Section: Introductionmentioning

confidence: 99%

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Diels‐Alder Reaction of Cyclopenta‐1,3‐diene and Anthracene to bis‐Fumarates Derived from Menthol Analogues

Piątek

Chapuis

2019

ChemistrySelect

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Due to steric interactions of the overly bulky substituted 8position, the classic 8-Ph-menthol (-)-1 d is not the optimal chiral auxiliary for the asymmetric Diels-Alder reaction of its bis fumarate (-)-2 d to dienes such as cyclopenta-1,3-diene 3 b, or anthracene 3 c. This prosthetic group (-)-1 d could efficiently be replaced by an intermediate smaller analog (-)-1 e, readily prepared in a single step by cyclopropanation of isopulegol (-)-1 b. This latter auxiliary, resulting from the industrial technology developed by Takasago for menthol (-)-1 a, does not necessitate the stereoselective ketone reduction and chromatographic separation of the usual Michael adducts, derived from (+)-pulegone. This chiral auxiliary (-)-1 e, never used as an asymmetric Diels-Alder promoter, is much more selective than menthol (-)-1 a itself, under uncatalyzed conditions, and is also more stable than the polymerizable isopulegyl derived dienophiles, under Lewis acid mediated conditions. This prosthetic group thus readily allows large scale operations in both accessible enantiomeric series. Results and DiscussionThe series of known chiral auxiliaries menthol (-)-1 a, [60][61] isopulegol (-)-1 b, [62][63][64] 8-Me-menthol (-)-1 c ([α] D 20 =-38.5, c = 1.0, CHCl 3 . For several signals, our 13 C-NMR attributions based [a]

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“…in 1963 in the same AlCl 3 mediated cycloaddition . (For ulterior [4+2] cycloadditions to buta‐1,3‐diene 3 a . For specific high pressure conditions ,.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Diels‐Alder Reaction of Cyclopenta‐1,3‐diene and Anthracene to bis‐Fumarates Derived from Menthol Analogues

Piątek

Chapuis

2019

ChemistrySelect

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Formation of Alkenes by Diels–Alder Reactions

Larock

2018

Comprehensive Organic Transformations

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General Reviews Regioselectivity Exo / Endo Selectivity Asymmetric Diels–Alder Reaction Mechanism Use of High Pressure Microwave Irradiation Infrared Irradiation Mechanical Ball Milling Ultracentrifugation Use of Ultrasound Catalysis Solvent Effects Cavity Effects Retro‐Diels–Alder Reaction Intramolecular Diels–Alder Reaction Inverse Electron‐Demand Diels–Alder Reaction Radical Cation Diels–Alder Reaction Ionic Diels–Alder Reaction Use of Heterodienophiles Use of Heteroatom‐Containing “Dienes” Use of Substituted 1,3‐Dienes o ‐Quinodimethanes and Heterocyclic Analogues Arynes and Hetarynes Some Other Dienophiles Dienophile Equivalents Transition Metal Carbenes as Dienophiles

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Asymmetric Diels—Alder Reaction of 1,3‐Butadienes with (—)‐Dimenthyl Fumarate in the Presence of BBr₃ and BBr₃×OEt₂.

Mamedov

2007

ChemInform

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Asymmetric Diels-Alder reaction of 1,3-butadienes with (−)-dimenthyl fumarate in the presence of BBr3 and BBr3·OEt2

Cited by 4 publications

References 3 publications

Diels‐Alder Reaction of Cyclopenta‐1,3‐diene and Anthracene to bis‐Fumarates Derived from Menthol Analogues

Diels‐Alder Reaction of Cyclopenta‐1,3‐diene and Anthracene to bis‐Fumarates Derived from Menthol Analogues

Formation of Alkenes by Diels–Alder Reactions

Asymmetric Diels—Alder Reaction of 1,3‐Butadienes with (—)‐Dimenthyl Fumarate in the Presence of BBr₃ and BBr₃×OEt₂.

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Asymmetric Diels-Alder reaction of 1,3-butadienes with (−)-dimenthyl fumarate in the presence of BBr3 and BBr3·OEt2

Cited by 4 publications

References 3 publications

Diels‐Alder Reaction of Cyclopenta‐1,3‐diene and Anthracene to bis‐Fumarates Derived from Menthol Analogues

Diels‐Alder Reaction of Cyclopenta‐1,3‐diene and Anthracene to bis‐Fumarates Derived from Menthol Analogues

Formation of Alkenes by Diels–Alder Reactions