The effect of alumina on the Diels-Alder reactions of cyclopentadiene with menthyl acrylate and dimenthyl fumarate.

Kabalka, George W.; Pagni, Richard M.; Bains, Satinder; Hondrogiannis, George; Plesco, Miechelle; Kurt, Robert; Cox, D. I.; Green, James

doi:10.1016/s0957-4166(00)80026-9

Cited by 32 publications

(10 citation statements)

References 25 publications

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“… a ) Isolated chemical yields from (‐)‐ 1 a ‐ f , respectively;,, b ) See; c ) see; d ) crude yield, ca . 77% yield after recrystallization;, e ) see;, f ) see; g ) see; h ) see; i ) (11 S ,12 S )‐ 7 exhibited [α] D 20 =‐44.8, c=1.0, CHCl 3 ; j ) overall selectivity after reduction of the diastereoisomer mixture.…”

Section: Introductionmentioning

confidence: 93%

“…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%

“…The diastereoselectivity for the uncatalyzed cycloaddition of (‐)‐ 2 a to cyclopenta‐1,3‐diene 3 b in toluene at 20 °C is extremely low (2‐5% d.e. ),, and in some instances may give opposite selectivity, depending on the solvent polarity ,. (In the case of 3 a , the sense of low induction in absence of Lewis acid may also depend on the temperature and pressure conditions) .…”

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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Section: Introductionmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

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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“…The menthyl derivative ( -)-Menthy1 acrylate (252) undergoes y-alumina-catalysed Diels-Alder cycloaddition with cyclopentadiene to give the endo-adduct in good diastereoisomeric excess.329. 330 A study has been made of the effect of variations in solvent on the rate, exolendo ratio, and diastereoselectivity of the same reaction. 331 The unsaturated menthyloxy lactone (253)62 has been developed as a chiral dienophile, affording adducts of up to 99% de.…”

Section: A H Hmentioning

confidence: 99%

Monoterpenoids

Grayson¹

1996

Nat. Prod. Rep.

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Cymbopogon coloratus Cymbopogon distans Cym bopogon t ra vanco rensis Egletes viscosa Erigeron canadensis Eucalyptus bicostata Eucalyptus brassiana S. T. Blake Eucalypt us b r idgesian a Eucalyptus camaldulensis Eucalyptus dealbata Eucalyptus delg up ta Eucalyptus torelliana Eupatorium adenophorum Spring. Ferulago sylvatica (Besser) Reichenb. Foeniculum vulgare Forsythia spp. Gardenia jasminoides Geranium robertianum Grindelia robusta Nutt. Grindelia squarrosa Dun. Hedychium coronarium Hedychium coronarium Koenig Hedychium odoratissimum Helichrysum picardii Heteropyxis natalensis Hjwopus oficinalis Juniperus sabina Kaunea longipetolia Lanata camara Lepechinia urbanii (Briq.) Epling Lepidophyllum quadrangulare (Meyen) Libanotis laticalycina Shan et Sheh. Liquidambar orientalis Mill. Litsea pungens Hemsl. Lonicera japonica Thunb. Magnolia coco (Lour) DC. Benth. and Hook.

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“…[6][7][8] We have tested this idea on the extensively studied Diels-Alder reaction [9][10][11][12][13][14][15][16] and Claisen rearrangement. [17][18][19][20][21][22][23] We have previously examined in detail the Diels-Alder reaction on thermally activated alumina, [24][25][26][27][28][29][30] but the Claisen rearrangement is new to us. The Claisen rearrangement of allyl phenyl ethers has been carried out on silica gel 31 and alumina.…”

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confidence: 99%

Microwave Activation of Alumina and its use as a Catalyst in Synthetic Reactions

Dadush

Green

Sease

et al. 2009

Journal of Chemical Research

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Microwave irradiation is a simple and efficient method of activating gamma alumina. Alumina activated in this manner is an excellent medium in which to carry out the Diels-Alder reaction and, in conjunction with additional microwave irradiation, the Claisen rearrangement. Several 2-allylphenols formed in the Claisen rearrangement rapidly undergo ring closure on alumina to form dihydrobenzofurans demonstrating the Brønsted acidity of the solid.

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The effect of alumina on the Diels-Alder reactions of cyclopentadiene with menthyl acrylate and dimenthyl fumarate.

Cited by 32 publications

References 25 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

Monoterpenoids

Microwave Activation of Alumina and its use as a Catalyst in Synthetic Reactions

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