52939-60-3Relevant articles and documents
Allylation of esters promoted by metallic dysprosium in the presence of mercuric chloride
Jia, Yu,Zhang, Mingfu,Tao, Fenggang,Zhou, Jingyao
, p. 2829 - 2835 (2002)
In the presence of mercuric chloride, the reactions of esters with allyl bromide and metallic dysprosium in anhydrous THF give diallyl alkyl carbinols in good yields. When γ-butyrolactone is used as the substrate, the corresponding product is 4-allyl-6-heptene-1, 4-diol.
A Selective and Functional Group-Tolerant Ruthenium-Catalyzed Olefin Metathesis/Transfer Hydrogenation Tandem Sequence Using Formic Acid as Hydrogen Source
Zieliński, Grzegorz K.,Majtczak, Jaros?awa,Gutowski, Maciej,Grela, Karol
, p. 2542 - 2553 (2018/03/09)
A ruthenium-catalyzed transfer hydrogenation of olefins utilizing formic acid as a hydrogen donor is described. The application of commercially available alkylidene ruthenium complexes opens access to attractive C(sp3)-C(sp3) bond formation in an olefin metathesis/transfer hydrogenation sequence under tandem catalysis conditions. High chemoselectivity of the developed methodology provides a remarkable synthetic tool for the reduction of various functionalized alkenes under mild reaction conditions. The developed methodology is applied for the formal synthesis of the drugs pentoxyverine and bencyclane.
Diastereotopic group selection in hydroxy-directed intramolecular C-H alkenylation of indole under oxidative palladium(II) catalysis
Kandukuri, Sandeep R.,Jiao, Lin-Yu,MacHotta, Axel B.,Oestreich, Martin
supporting information, p. 1597 - 1609 (2014/06/09)
Group-selective palladium(II)-catalyzed ring closures involving C-H bond alkenylation are reported. The cyclization precursors contain a prochiral bis(homoallylic) alcohol unit tethered to either an arene or an indole. The homobenzylic hydroxy group in these substrates is positioned to act as a directing group in the ortho-selective C-H bond activation prior to the cyclization event. Arene-derived precursors reacted poorly, even when applying a protocol that had proven effective in intermolecular hydroxy-directed C-H bond alkenylations. No asymmetric induction was obtained with chiral ligands, mono-N-protected amino acids (MPAAs) in particular. Conversely, the cyclization of indole-derived precursors was substantially more efficient, and installation of a substituent in the benzylic position rendered these intramolecular C-H bond alkenylations diastereoselective. The diastereotopic group selection is high with diastereomeric ratios ranging from dr=91:9 to 94:6.
An efficient of Grignard-type procedure for the preparation of gem-diallylated compound
Shen, Kao-Hsien,Kuo, Chun-Wei,Yao, Ching-Fa
, p. 6348 - 6351 (2008/02/12)
An efficient and a new procedure for the conversion of various carboxylic acid derivatives into the corresponding gem-diallylated compound under mild reaction condition has been developed. The triallylaluminum mediated Grignard-type addition of carboxylic acid derivative was utilized as a key operation to affect the transformation. The procedure is operationally simple, giving good to excellent product yields for a broad range of substrates. The chemoselectivity and regioselectivity of triallylaluminum were also demonstrated.
Gem-diallylation of acyl azides with allylsamarium bromide under mild conditions
Li, Jian,Liu, Yongjun,Zhang, Yongmin
, p. 438 - 439 (2007/10/03)
Allylsamarium bromide reacts with acyl azides to give the corresponding gem-diallylation products, 4-alkyl-1,6-heptadienes-4-ols (3), in good to excellent yields. This novel reaction proceeds readily within a few minutes at room temperature.
Organosamariums: Preparation using diiodosamarium and reactivity in tetrahydropyran
Hamann-Gaudinet, Beatrice,Namy, Jean-Louis,Kagan, Henri B.
, p. 39 - 47 (2007/10/03)
Diiodosamarium prepared in tetrahydropyran reduces allylic, benzylic and alkyl halides at 0 or -15°C to give organosamariums which are stable under these conditions. The reactivity of these organometallics has been explored, showing that they are very sel
Generation and reactivity of allylic and benzylic samarium compounds using diiodosamarium in tetrahydropyran
Hamann-Gaudinet, Beatrice,Namy, Jean-Louis,Kagan, Henri B.
, p. 6585 - 6588 (2007/10/03)
Diiodosomarium prepared in THP reduces allylic iodides and bromides at 0 or -15°C to give organosamarium compounds which ore stable under these conditions. These allylic samarium compounds react with many functionalities including the keto group of keto esters. Benzylic samarium compounds were prepared similarly from benzylic bromides.
172. β-Cleavage of Bis(homoallylic) Potassium Alkoxides. Two-Step Preparation of Propenyl Ketones from Carboxylic Esters. Synthesis of ar-Turmerone, α-Damascone, β-Damascone, and β-Damascenone
Snowden, Roger L.,Linder, Simon M.,Muller, Bernard L.,Schulte, Karl H.
, p. 1858 - 1878 (2007/10/02)
The transformation of 36 bis(homoallylic) alcohols VII to alkenones IX and X via β-cleavage of their potassium alkoxides VIIa in HMPA has been investigated (cf.Scheme 2).These studies have established an order of β-cleavage for 2-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1,1-dimethyl-2-propenyl, and benzyl groups in alkoxides 49a-56a and have allowed a comparison between the β-cleavage reaction and the oxy-Cope rearrangement in alkoxides 74a-83a.As illustrative synthetic applications, a two-step preparation of propenyl ketones 15-42 from carboxylic esters is described, together with syntheses of ar-turmerone (48), α-damascone ((E)-71), β-damascone ((E)-109), and β-damascenone ((E)-111).
FRAGMENTATION OF HOMOALLYLIC ALKOXIDES. SYNTHESIS OF PROPENYL and 2-METHYLPROPENYL KETONES FROM CARBOXYLIC ESTERS
Snowden, Roger L.,Muller, Bernard L.,Schulte-Elte, Karl H.
, p. 335 - 338 (2007/10/02)
An efficient two-step synthesis of propenyl and 2-methylpropenyl ketones from carboxylic esters is described which uses as the key step the fragmentation of a potassium dihomoallylic alkoxide under mild thermolytic conditions.
