Preparation and Diels-Alder Reactions of Hetero-Substituted 1,3-Dienes

Petrzilka, Martin; Grayson, J. Ian

doi:10.1055/s-1981-29592

Cited by 213 publications

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“…This trend of reactivity has also been observed in the reaction with maleic anhydride (12), although in this case the observation of the preferential stereoselectivity exerted by a trans dienophile was precluded. To the best of our knowledge, no studies on the stereoselectivity in the cycloaddition to 2-oxy substituted 1,3-cyclodienes have been reported (15).…”

Section: [41 -Productsmentioning

confidence: 99%

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Synthesis, stereochemistry, and transformations of (E)-1,2-bis(benzenesulfonyl)ethylene cycloadducts to 2-oxa substituted 1,3-dienes

Lucchi¹,

Lucchini²,

Zamai³

et al. 1984

Can. J. Chem.

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This paper is dedicated to Professor Peter Yates on the occasion of his 60th birthdayOTTORINO DE LUCCHI, VITTORIO LUCCHINI, MORENO ZAMAI, GIORGIO MODENA, and GIOVANNI VALLE. Can. J. Chem. 62, 2487 (1984).The cycloaddition of (E)-l,2-bis(benzenesulfonyl)ethylene (2) to 2-acetoxy-and 2-silyloxy-l,3-cyclodienes occurs in high yields and with high steroselectivity. Structure assignment has been based largely on 'H nrnr nuclear Overhauser effect (nOe) experiments on the isolated products. The cycloadducts 4a and 4b derived from the 2-oxa substituted cyclopentadienes have been further elaborated to the parent norbornenone, to the respective unsaturated sulfones 5 , and to the P-hydroxy substituted sulfone 6. The vinyl sulfones 5 have also been independently synthesized via cycloaddition of benzenesulfonyl acetylene. The sulfones obtained are potentially important starting molecules for the preparation of more complex targets.O-ITORINO DE LUCCHI, VIITORIO LUCCHINI, MORENO ZAMAI, GIORGIO MODENA et GIOVANNI VALLE. Can. J. Chem. 62, 2487(1984.La cycloaddition du (E)-bis(benz&nesulfonyl)-1,2-Cthylbne (2) sur les acCtoxy-2 et silyloxy-2 cyclodibnes-1,3 se produit avec des rendements ClevCs et avec une stCrCosClectivitC ClevCe. La dktermination des structures repose principalement sur des expCriences d'effet Overhauser nuclCaire (eon) et rmn du 'H qui ont Ct C rCalisCes sur les produits isolCs. De plus, une filiation a pu Ctre Ctabli entre les cycloadduits 4a et 4b, obtenus A partir des oxa-2 cyclopentadibnes, et la norbornCnone apparentke ainsi qu'avec la sulfone insaturie 5 et la P-hydroxysulfone 6. Faisant appel i une cycloaddition du benzbnesulfonylacCtylbne,

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Section: [41 -Productsmentioning

confidence: 99%

“…The residue is flash chromatographed through a silica gel column (>230 mesh, weight ratio adsorbant/substrate ca. 15 …”

Section: Preparation Ofmentioning

confidence: 99%

Synthesis, stereochemistry, and transformations of (E)-1,2-bis(benzenesulfonyl)ethylene cycloadducts to 2-oxa substituted 1,3-dienes

Lucchi¹,

Lucchini²,

Zamai³

et al. 1984

Can. J. Chem.

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“…The syntheses of heterosubstituted 1,3-butadienes [2] are well established, allowing access to specifically functionalized reagents for the production of cyclic structures with complex substitution patterns. Furthermore, asymmetric activating substituents have shown remarkable success in achieving diastereoselectivity in [4 + 2] cycloaddition reactions and, when labile, allow for the recovery of chiral auxiliaries [3,4] .…”

Section: Introductionmentioning

confidence: 99%

Diels - Alder Reactions of 3-Furylamines in Organic and Aqueous Solvents

2006

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“…Recent advances in the comprehension of electronic and steric effects governing this reaction3 have been accompanied by the use of new specifically functionalized dienes and dienophiles to produce hitherto unattainable substitution patterns both regioselectively and s t e r e o s e l e~t i v e l~.~ The introduction of one or more hetero substituents on the diene invariably has an effect o n the regiochemistry of the cycloaddition and permits further transformations of the adducts that take advantage of the relationship between the hetero substituents and the newly formed c a r b o n~a r b o n double bonds. For example silyloxy-substituted butadienes (13)(14)(15) have come into widespread use in natural product syntheses. Unfortunately, these types of dienes and the cycloaddition products derived from them are rather labile under acidic or basic conditions, or even in polar solvents.…”

Section: Introductionmentioning

confidence: 99%

Lewis acid catalyzed Diels–Alder reactions of two useful dienyl phosphate esters

Liu¹,

Feng²,

Kim³

et al. 1994

Can. J. Chem.

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. The Lewis acid catalyzed Diels-Alder reactions of dienyl phosphate esters 1 and 2 were examined. 2-Diethylphosphoryloxy-1,3-butadiene (1) was found to react with a variety of a$-unsaturated carbonyl compounds under Lewis acid catalysis with excellent regioselectivity to give synthetically useful cyclohexene derivatives. The adducts were produced in accordance with the normal rules governing the Diels-Alder addition. In the presence of stannic chloride acyclic a$-unsaturated ketones such as ethyl vinyl ketone and methyl vinyl ketone reacted rapidly with diene phosphate 1 to give exclusively thepara-addition products 8 and 9 in excellent yields. When diene 1 was treated with the complex cyclic enone ester 14 in the presence of ferric chloride the single para-rule adduct 15 was obtained in good yield. The stannic chloride catalyzed Diels-Alder reactions of trans-2-diethylphosphoryloxy-l,3-pentadiene (2) were also studied. Diene phosphate 2 reacted efficiently with a number of acyclic a$-unsaturated ketones such as methyl vinyl ketone, ethyl vinyl ketone, and trans-3-penten-2-one with complete regio-and stereoselectivity to give single cyclohexene derivatives 38,39, and 40.HSWG-JANG Lnr, WAISENG MARTIN FENG, JEUNG BEA KIM et ERIC N.C. BROWNE. Can. J. Chem. 72,2163Chem. 72, (1994. On a ttudit les rtactions de Diels-Alder catalystes par les acides de Lewis des esters 1 et 2, phosphates de ditnyle. On a trouvt que, sous catalyse par les acides de Lewis, le 2-diithylphosphoryloxybuta-1,3-dibne (1) rtagit avec une varittt de composts carbonylts ol$-insaturts avec une excellent rtgiostlectivitt pour conduire B des dtrivts du cyclohexbne qui sont utiles en synthbse. Les adduits se produisent selon les rbgles normales gouvernant les additions de Diels-Alder. En prtsence de chlorure stannique, les cttones u,p-insaturtes, telles que l'tthyl vinyl cttone et la mtthyl vinyl cttone, rtagissent rapidement avec le phosphate ditnique 1 pour donner exclusivement les produits d'additionpara, 8 et 9, avec d'excellents rendements. Lorsqu'on traite le dibne 1 avec l'ester cyclohextnonique complexe 14, en prisence de chlorure ferrique, seul l'adduit para, 15, a ttt obtenu avec un bon rendement. On a aussi ttudit les rtactions de Diels-Alder catalystes par le chlorure stannique du trans-2-ditthylphosphoryloxybuta-1,3-dibne (2). Le phosphate diinique 2 rtagit d'une f a~o n efficace avec un certain nombre de cttones a,p-insaturtes, telles que la mtthyl vinyl cttone, l'tthyl vinyl cttone et la trans-pent-3-tn-2-one, avec des rtgio-et sttrtostlectivitts complbtes pour donner uniquement les dtrivts cyclohextniques 38,39 et 40.[Traduit par la rtdaction]

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Preparation and Diels-Alder Reactions of Hetero-Substituted 1,3-Dienes

Cited by 213 publications

References 0 publications

Synthesis, stereochemistry, and transformations of (E)-1,2-bis(benzenesulfonyl)ethylene cycloadducts to 2-oxa substituted 1,3-dienes

Synthesis, stereochemistry, and transformations of (E)-1,2-bis(benzenesulfonyl)ethylene cycloadducts to 2-oxa substituted 1,3-dienes

Diels - Alder Reactions of 3-Furylamines in Organic and Aqueous Solvents

Lewis acid catalyzed Diels–Alder reactions of two useful dienyl phosphate esters

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