EurekaMag.com logo
+ Site Statistics
References:
53,517,315
Abstracts:
29,339,501
+ Search Articles
+ Subscribe to Site Feeds
EurekaMag Most Shared ContentMost Shared
EurekaMag PDF Full Text ContentPDF Full Text
+ PDF Full Text
Request PDF Full TextRequest PDF Full Text
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter
Follow on Google+Follow on Google+
Follow on LinkedInFollow on LinkedIn

+ Translate

Syntheses of alpha beta unsaturated ketones starting from vinylic and allylic grignard reagents via 2 imidazolylmethanol intermediates



Syntheses of alpha beta unsaturated ketones starting from vinylic and allylic grignard reagents via 2 imidazolylmethanol intermediates



Heterocycles (Tokyo) 27(2): 457-474



Various .alpha.,.beta.-unsaturated ketones (9, 12 and 16) were prepared from 2-alkanol-1-methyl-1H-imidazoles (6, 10 and 13, respectively), which were obtained by treatment of 2-acyl-1-methyl-1H-imidazoles (1) with vinylic Grignard reagents, a lithium acetylide and allylic Grignard reagents, respectively. dl-(ar)-Turmerone (16i) was also synthesized as an application of the present methodology.

(PDF 0-2 workdays service: $29.90)

Accession: 006559644

Download citation: RISBibTeXText



Related references

Asymmetric syntheses using tert-leucine. 1. An asymmetric synthesis of beta-substituted aldehydes via 1,4-addition of Grignard reagents to chiral alpha, beta-unsaturated aldimines. Journal of the American Chemical Society 98(23): 7450-7459, 1976

Benzotriazole- and 1,2,4-Triazole-Stabilized Allylic Anions: Applications in Syntheses of Functionalized alpha,beta-Unsaturated Ketones, gamma-Lactones, gamma-Lactams, and beta-Substituted Esters. Journal of Organic Chemistry 62(3): 706-714, 1997

Studies On Steroidal Compounds. Xii. Sterochemistry Of 1,4-Addition Of Grignard Reagent For Alpha,beta-Unsaturated Steroidal Ketones. Grignard Reaction Of 3-Beta-Hydroxycholest-4-En-6-One. Chemical & Pharmaceutical Bulletin 12: 1224-1231, 1964

General synthetic routes to alpha beta unsaturated carboxylic esters and ketones via the 3 3 sigmatropic rearrangement of allylic thione carbamates stereospecific syntheses of 2 ant mandibular gland secretions. Tetrahedron Letters (32): 2895-2898, 1978

Highly efficient and stereoselective access to -alpha,beta-difluoroallyl alcohols and -alpha-fluoro-alpha,beta-unsaturated aldehydes based on the reaction of 2,3,3-trifluoro-1-propenyl p-chlorobenzenesulfonate with Grignard reagents. Tetrahedron Letters 39(14): 1913-1916, April 2, 1998

The addition of the Grignard reagent to hindered alpha, beta-unsaturated ketones. 1945

Reaction of alkyl and aryl Grignard reagents with trifluoroacetyldihydropyrans and other cyclic beta-alkoxy-alpha,beta-unsaturated trifluoromethylketones. Tetrahedron 56(51): 10039-10055, 15 December, 2000

Allylic rearrangement of cyanophosphate. II Synthesis of .BETA.-cyano-.ALPHA.,.BETA.-unsaturated ketones. Chemical & Pharmaceutical Bulletin 34(7): 2747-2753, 1986

Synthesis and Reactions of Allylic, Allenic, Vinylic, and Arylmetal Reagents from Halides and Esters via Transient Organopalladium Intermediates. Chemical Reviews 100(8): 3163-3186, 2001

NaOH-catalyzed thiolysis of alpha,beta-epoxyketones in water. A key step in the synthesis of target molecules starting from alpha,beta-unsaturated ketones. Journal of Organic Chemistry 69(7): 2315-2321, 2004

Catalytic asymmetric conjugate addition of grignard reagents to alpha,beta-unsaturated sulfones. Organic Letters 10(19): 4219-4222, 2008

Conjugate addition of grignard reagents to alpha beta unsaturated esters preparation of alkylsilylketeneacetals. Tetrahedron 47(39): 8331-8338, 1991

Chemoselective reduction of complex alpha,beta-unsaturated ketones to allylic alcohols over Ir-metal particles on beta zeolites. Angewandte Chemie 42(43): 5333-5336, 2003

The Reaction of Enaminones with Grignard Reagents: Synthesis of α,β-Unsaturated Ketones. Synthetic Communications 28(10): 1743-1753, 1998

Copper-catalyzed enantioselective conjugate addition of Grignard reagents to alpha,beta-unsaturated esters. Angewandte Chemie 44(18): 2752-2756, 2005