60523-21-9Relevant academic research and scientific papers
Enzyme-mediated optical resolution of 2-methyl-3,4-pentadien-1-ol, a chiral building block possessing terminal allenyl group
Konegawa, Tadayoshi,Ohtsuka, Yoshikazu,Ikeda, Hajime,Sugai, Takeshi,Ohta, Hiromichi
, p. 1297 - 1299 (1997)
Both enantiomers (>95% e.e.) of 2-methyl-3,4-pentadien-1-ol, a chiral building block possessing a terminal allenyl group were prepared via the two-stage enzymatic kinetic resolution, i.e., a sequence of lipase-catalyzed acetylation (Pseudomonas cepacia) and hydrolysis (Candida antarctica).
Palladium-Catalyzed Stereoselective Cyclization of in Situ Formed Allenyl Hemiacetals: Synthesis of Rosuvastatin and Pitavastatin
Spreider, Pierre A.,Breit, Bernhard
supporting information, p. 3286 - 3290 (2018/06/11)
A diastereoselective palladium-catalyzed cyclization of allenyl hemiacetals is described. It permits the selective synthesis of 1,3-dioxane derivatives, precursors for syn-configured 1,3-diols which make an appearance in all of the statin representatives. The reaction allows the total synthesis of Rosuvastatin and Pitavastatin in a straightforward fashion.
Synthesis of two nuphar alkaloids by allenic hydroxylamine cyclisation
Bates, Roderick W.,Lim, Chia Juan
scheme or table, p. 866 - 868 (2010/06/11)
A highly diastereoselective silver-catalysed cyclisation of a 2-substituted β-allenic hydroxylamine is reported. The resulting trans-isoxazolidine is converted into two Nuphar alkaloids by a sequence involving cross-metathesis and intramolecular reductive amination. Georg Thieme Verlag Stuttgart - New York.
Efficient synthesis of 4-(2′-alkenyl)-2,5-dihydrofurans and 5,6-dihydro-2H-pyrans via the Pd-catalyzed cyclizative coupling reaction of 2,3- or 3,4-allenols with allylic halides
Ma, Shengming,Gao, Wenzhong
, p. 6104 - 6112 (2007/10/03)
In the absence of a base, palladium(II) catalysts, such as PdCl2, PdCl2(CH3CN)2, Pd(OAc)2, and [(π-C3H5)PdCl]2, can catalyze the cyclizative coupling reaction of 2,3- or 3,4-allenols with allylic halides in DMA at room temperature to provide 2,5-dihydrofurans and 5,6-dihydro-2H-pyrans, respectively, in moderate to good yields. Under similar reaction conditions, nonsubstituted 2,3-allenol 1s affords bimolecular cyclizative coupling product 5s as the major product. The scope of the reaction and its mechanism have been studied briefly. On the basis of the experimental results, the transformation was believed to proceed via a divalent palladium-catalyzed pathway.
Silver(I)-catalyzed aminocyclization of 2,3-butadienyl and 3,4-pentadienyl carbamates: An efficient and stereoselective synthesis of 4-vinyl-2-oxazolidinones and 4-vinyltetrahydro-2H-1,3-oxazin-2-ones
Kimura,Tanaka,Tamaru
, p. 1689 - 1705 (2007/10/02)
Silver(I) salts in combination with an appropriate base (mostly triethylamine) catalyzed the aminocyclization of N-substituted 2,3-butadienyl carbamates 1 (benzene, 50°C) to provide 4-vinyl-2-oxazolidinones 2 in good yields. The stereoselectivity (trans-2/cis-2) ranged from 1.4 for C5-Me to >30 for C5-phenyl, isopropenyl, and t-butyl derivatives. 3,4-Pentadienyl tosylcarbamates 3, the one-carbon higher homologues of 1, underwent a similar cyclization to give 4-vinyltetrahydro-2H-1,3-oxazin-2-one 4 in synthetically useful yields and in higher trans selectivities than 1.
Novel flavoring compositions and products containing isomer mixtures containing high proportions of 2-methyl-cis-3-pentenoic acid
-
, (2008/06/13)
Methods are described for producing mixtures containing greater than 50% 2-methyl-cis-3-pentenoic acid as well as substantially pure 2-methyl-cis-3-pentenoic acid for preparing foodstuffs, flavoring compositions for foodstuffs, chewing gum compositions, flavoring compositions for chewing gum, medicinal product compositions and ingredients for medicinal product compositions by including therein the isomeric mixtures containing greater than 50% cis-2-methyl-3-pentenoic acid produced by the above-stated processes in order to produce in foodstuff flavorings, medicinal product flavorings and chewing gum flavorings, a sweet, fruity, strawberry, winey-cognac, butter-like, rum-like and butterscotch aroma and a sweet, strawberry, nutty-coconut, fatty, butter-like, rum-like and butterscotch-like taste with fruity, coconut-like isovaleric undertones.
