86542-09-8Relevant articles and documents
Chirality and fragrance chemistry: Stereoisomers of the commercial chiral odorants muguesia and pamplefleur
Abate, Agnese,Brenna, Elisabetta,Fuganti, Claudio,Gatti, Francesco G.,Giovenzana, Tommaso,Malpezzi, Luciana,Serra, Stefano
, p. 1281 - 1290 (2007/10/03)
(Chemical Equation Presented) The work describes the enzyme-mediated preparation and the odor evaluation of the single stereoisomers of the commercial odorants Muguesia and Pamplefleur. The synthetic approach to Muguesia stereoisomers helped to clear the assignment of the relative configuration of intermediate diols 5. The odor response of Pamplefleur isomers was found to be rather unusual. No stereoisomer prevailed, but each one played a definite role in establishing the odor sensation of the final blend.
Highly diastereoselective aldol synthesis from α-iodo ketones in aqueous media
Shibata, Ikuya,Kawasaki, Masatsugu,Yasuda, Makoto,Baba, Akio
, p. 689 - 690 (2007/10/03)
Highly diastereoselective aldol synthesis from α-iodo ketones was promoted under aqueous conditions by a distannane system, (n-Bu3Sn)2, n-Bu2SnF2 and HMPA. Aqueous solutions of acetaldehyde, formaldehyde and piv
REDUCTION OF DELTA 2-ISOXAZOLINES. PART 3: RANEY-NICKEL CATALYZED FORMATION OF beta -HYDROXY KETONES.
Curran
, p. 5826 - 5833 (2007/10/02)
The importance of the beta -hydroxy ketone moiety has led to the development of a wide variety of aldol type methodologies for its construction. A conceptually new approach to these 'aldol adducts' is presented on the basis of left bracket 3 plus 2 right bracket dipolar cycloaddition of in situ generated nitrile oxides and olefins followed by reduction of the resulting DELTA **2-isoxazolines. This approach provides a nice complement of the aldol type reaction. Optimum conditions for the transformation of DELTA **2-isoxazolines to beta -hydroxy ketones use Raney-nickel catalyst, boric acid, 5/1 MeOH/H//2O, and hydrogen gas. Under these mild conditions, 3-methyl-5-n-butyl- DELTA **2-isoxazoline is transformed to 4-hydroxy-2-octanone in high yield. Thus 'directed aldol' type adducts are readily available by selection of the appropriate olefin and nitrile oxide precursor (usually the 1 degree nitro compound).
Prins Reactions of Arylaldehydes, V: On the Reaction with 2-Butene and with Cyclohexene
Griengl, Herfried,Mayer, Arnulf,Geppert, Klaus Peter
, p. 1007 - 1016 (2007/10/02)
By reaction of 2--2-phenyl-1,3-dithiane (1a) with cis-2-butene oxide, subsequent reduction and acetalization c-4,t-5-dimethyl-r-2,c-6-diphenyl-1,3-dioxane (3a) and t-4,c-5-dimethyl-r-2,c-6-diphenyl-1,3-dioxane (3b) were synthesized as model compounds.For the same purpose by aldol reaction of cyclohexanone and reduction (1RS,2SR)-2cyclohexanol (7a), (1RS,2RS)-2cyclohexanol (8a), and (1RS,2RS)-2cyclohexanol (8b), and by acetalization (2α,4α,4aβ,8aβ)-2,4-bis(4-methoxyphenyl)hexahydro-4H-1,3-benzodioxin (9a) and (2α,4α,4aα,8aβ)-2,4-bis(4-nitrophenyl)hexahydro-4H-1,3-benzodioxin (10b) were obtained.From Prins reactions, starting with 2-butene 3a, c-4,c-5-dimethyl-r-2,c-6-diphenyl-1,3-dioxane (3c), r-4,t-5-dimethyl-c-6-phenyl-1,3,2-dioxathiane-2,2-dioxide (4), and (2Z,4E)-1,5-diphenyl-4-methyl-2,4-pentadien-1-on (5), and starting with cyclohexene (E)-3-(4-methoxybenzylidene)cyclohexenyl-4-methoxyphenyl ketone (11) have been isolated in low yields. - Keywords: Addition reactions; 1,3-Diols; 1,3-Dioxanes