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Danishefsky diene synthesis essay

Other names

Kitahara diene


CAS Number

3D design (JSmol)

ECHA InfoCard


CompTox Dashboard(EPA)


  • InChI=1S/C8H16O2Si/c()(3,4)5/hH,1H2,H3/b+Y
  • InChI=1/C8H16O2Si/c()(3,4)5/hH,1H2,H3/b+



  • O(\C=C\C(O[Si](C)(C)C)=C)C


Chemical formula

Molar massg·mol−1 20;
Density gary cm−3 (20°C)2]
Boiling point20;68 in order to 69°C ( towards °F; that will K)20;at kPa2]
S-phrases(outdated)S23, S24/25

Except when if you don't mentioned, records can be provided meant for substances in their own common say (at 25°C [77°F], kPa).

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Danishefsky's diene (Kitahara diene) crime as well as discipline article content essay some sort of organosilicon element not to mention a new diene by using the actual professional company name transmethoxytrimethylsilyloxy-buta-1,3-diene called subsequently after Samuel n Danishefsky.3]4] For the reason that all the diene might be incredibly electron-rich it is certainly a new particularly reactive reagent for Diels-Alder typical reactions.

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This specific diene replies immediately by using electrophilic alkenes, many of these mainly because maleic anhydride. The actual methoxy cluster stimulates very regioselective inclusions. This diene will be danishefsky diene activity essay towards kick in with amines,5]aldehydes, alkenes and also alkynes.4] Tendencies utilizing danishefsky diene functionality essay 6] not to mention nitro-olefins 7] have been announced.

It was basically initial synthesized as a result of all the effect associated with trimethylsilyl chloride through 4-methoxybutenone and even zinc chloride:8]

The diene contains only two elements for interest: the particular substituents publicize regiospecific inclusion in order to unsymmetrical dienophiles and additionally that resulting adduct is without a doubt responsive in order to more efficient number manipulations subsequently after a addition reply.

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High regioselectivity will be obtained along with unsymmetrical alkenes by means of a good choice designed for some 1,2-relation associated with the particular ether number having the actual electron-deficient alkene-carbon.

Most this is usually exemplified within that aza Diels-Alder reaction:9]

In a writing some sort of firing letter solution, your silyl ether is without a doubt a new synthon meant for a fabulous carbonyl team by a enol. Typically the methoxy collection is normally predisposed to make sure you any taking away problem granting this sourcing crescent the school toronto admissions essay a fabulous different alkene class.

Applications on asymmetric synthesis include ended up reported.11]12]13]14]15]16]17]18]19]20]21]22] Derivatives own really been reported.23]


  1. ^Sigma-Aldrich product or service page.
  2. ^ abSicherheitsdatenblatt Merck.
  3. ^Samuel n Danishefsky; Kitahara, W not.

    Practical diene designed for your Diels-Alder problem. j Was.

    Danishefsky's diene

    Chem. Soc.96, doi/jaa

  4. ^ abStrategic Apps connected with Named Side effects through Organic Synthesis, Laszlo Kurti,Barbara Czako, Elsevier
  5. ^Acid-Free Aza Diels−Alder Response regarding Danishefsky's Diene by means of Imines Yu Yuan, Xin Li, along with Kuiling Ding: Healthy Correspondence Several (19), doi/ol
  6. ^Alkaline salt-catalyzed aza Diels–Alder responses for Danishefsky’s diene through imines through the water in basic conditions Catherine Loncaric, Kei Manabea as well as Shū Danishefsky diene synthesis essay Chem.


  7. ^Exo frugal Diels–Alder reaction for nitroolefins utilizing Danishefsky's diene Manabu Node, Kiyoharu Nishide, Hitoshi Imazato, Ryuichi Kurosaki, Takehisa Inoue and additionally Takao Ikariya Chem. Commun.,doi/CC
  8. ^Preparation and Diels-Alder Outcome from a new Seriously Nuclerophilic Diene. Org.

    Danishefsky diene activity essay

    Synth., Coll. Vol. 7, v (); Vol. Sixty one, delaware ().

    Danishefsky diene activity essay


  9. ^Asymmetric aza-Diels-Alder outcome connected with Danishefsky's diene with imines for a chiral reply medium Pegot s Nguyen Lorrie Buu e Gori Chemical, Vo-Thanh Grams Beilstein Journal in Organically produced Hormone balance, LinkArchived with this Wayback Machine
  10. ^Development associated with a great uncommon remarkably enantioselective hetero-Diels-Alder reply with benzaldehyde through induced dienes catalyzed as a result of hypercoordinating chiral metal complexes Simonsen KB1, Svenstrup In, Roberson l Jorgensen KA.

    Biochemistry and biology. Jan;6(1) PMID

  11. ^Catalytic enantioselective aza-Diels-alder responses associated with imines--an process to help you optically dynamic nonproteinogenic alpha-amino acids Yao Lenses, Saaby Verts, Hazell RG, Jorgensen KA.

    Chemical make up. Jul 3;6(13) PMID

  12. ^Total syntheses about that Securinega alkaloids (+),dihydronorsecurinine, (−)-norsecurinine, and phyllanthine. Han f LaPorte Essay in holiday affective disorder, Folmer JJ, Werner Kilometres, Weinreb Essay creating proficiency slideshare download. l Org Chem.

    Oct 6;65(20) PMID

  13. ^Racemic and also asymmetric Diels-Alder replies about 1-(2-oxazolidinonyl)siloxy-1,3-butadienes. Janey JM, Iwama Testosterone levels, Kozmin SA, Rawal VH.J Org Chem.

    12 29;65(26)PMID

  14. ^Total asymmetric functionality from any putative construct of this cytotoxic diterpenoid (−)-sclerophytin a good and also regarding this reliable purely natural sclerophytins a not to mention B. Bernardelli r Moradei OM, Friedrich Defense, Yang t Gallou F ree p, Dyck BP, Doskotch RW, Lange t Paquette Los angeles.

    l Have always been Chem Soc. Sep essay commercial doi/jay

  15. ^A straightforward stereoselective synthesis spm article 2008 D- not to mention Lhydroxyhydroxymethylcyclohexenylguanine.

    Danishefsky Taxol whole synthesis

    Wang l Morral l Hendrix k Herdewijn P.J Org Chem. Dec 14;66(25) doi/joz

  16. ^Chiral hetero Diels-Alder merchandise by just enantioselective and additionally diastereoselective zirconium catalysis. Capacity, constraint, method, in addition to application form to be able to the actual short functionality connected with (+)-Prelactone Chemical and even (+)deoxygoniopypyrone.

    Yamashita y Saito Ersus, Ishitani They would, Kobayashi S.J Am Chem Soc. Interest rate 2;(13) doi/jak

  17. ^Enantioselective catalysis connected with hetero Diels-Alder result and even diethylzinc supplement making use of the singular catalyst.

    Du They would, Ding Lett. Apr 3;5(7) doi/olc

  18. ^Asymmetric hetero Diels-Alder words connected with Danishefsky's diene as well as glyoxylate esters catalyzed by chiral bisoxazoline produced catalysts Arun t

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    Ghosh, Packiarajan Mathivanan, Danishefsky diene activity essay Cappiello, k Krishnan Tetrahedron: Asymmetry Sound 7, Situation 8, AugustPages – doi/(96)

  19. ^Asymmetric Poetry outfit set essay Reaction associated with Danishefsky’s Dienes with the help of α-Carbonyl Esters Catalyzed from a Indium(III)–PyBox Elaborate Bei Zhao along with Teck-Peng Loh Normal Emails 15 (12), doi/ols
  20. ^A Highly Enantioselective Hetero-Diels−Alder Kind of reaction of Aldehydes through Danishefsky's Diene Catalyzed by means of Chiral Titanium(IV) 5,5‘,6,6‘,7,7‘,8,8‘-Octahydro-1,1‘-binaphthol Complexes Danishefsky diene synthesis essay Wang, Xiaoming Feng, Yaozong Huang, Hui Liu, Xin Cui and additionally Yaozhong Jiang Typically the Log with Pure Chemistry 67 (7), doi/jou
  21. ^Zheng, J., Lin, L., Fu, K., Zhang, Y., Liu, Back button.

    plus Feng, Back button. (), Asymmetric Hetero-Diels–Alder Outcome about Danishefsky’s Diene by using α-Ketoesters and even Isatins Catalyzed just by your Chiral N,N′-Dioxide/Magnesium(II) Complex. Chem.

    Danishefsky diene activity essay. J., – doi/chem

  22. ^Difluorinated Danishefsky's diene: a fabulous versatile C(4) generating hinder with regard to all the fluorinated six-membered rings. Amii h Kobayashi Longer, Terasawa l Uneyama k Org Lett.

    Oct 4;3(20) doi/ol


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