21944-96-7Relevant articles and documents
DIASTEREOSELECTIVE SYNTHESIS OF (E)-ALKENES AND (E)-1,ω-DIENES STARTING FROM DIASTEREOISOMERIC MIXTURES OF l-BROMO-l-ALKENES : NEW SYNTHESES OF MONOUNSATURATED OR BRIDGED RING-KETAL NATURALLY OCCURRING SUBSTANCES.
Rossi, Renzo,Carpita, Adriano
, p. 2529 - 2532 (1986)
The PdCl2(dppf)-catalyzed cross-coupling reaction between diastereoisomeric mixtures of l-bromo-l-alkenes which contain n equiv. of (E)-stereoiomers and n equiv. of Grignard reagents allows to obtain (E)-alkenes or (E)-l,ω-dienes having 95.5-99percent stereoisomeric purity in satisfactory yields.Such compounds are useful precursors to several naturally occurring substances.
Alkenyl Carbonyl Derivatives in Enantioselective Redox Relay Heck Reactions: Accessing α,β-Unsaturated Systems
Zhang, Chun,Santiago, Celine B.,Kou, Lei,Sigman, Matthew S.
, p. 7290 - 7293 (2015)
A highly enantioselective and site-selective Pd-catalyzed arylation of alkenes linked to carbonyl derivatives to yield α,β-unsaturated systems is reported. The high site selectivity is attributed to both a solvent effect and the polarized nature of the carbonyl group, both of which have been analyzed through multidimensional analysis tools. The reaction can be performed in an iterative fashion allowing for a diastereoselective installation of two aryl groups along an alkyl chain.
Simple Synthesis of (Z)-12-Nonadecen-9-one, (Z)-13-Icosen-10-one, the Sex Pheromone of Peach Fruit Moth, and (Z)-5-Undecen-2-one, a Biologically Active Molecule from the Pedal Gland of the Bontebok
Yamashita, Masakazu,Matsumiya, Kaoru,Murakami, Kotomi,Suemitsu, Rikisaku
, p. 3368 - 3370 (1988)
A simple and convenient synthesis of (Z)-12-nonadecen-9-one, (Z)-13-icosen-10-one, the sex pheromone of the peach fruit moth, and (Z)-undecen-2-one, the pheromone from the pedal gland of the bontebok, is described.These pheromones were readily synthesized using succesive alkylation of acetone dimethylhydrazone in one-pot.
SYNTHESIS OF cis-UNDEC-5-en-2-one - THE PHEROMONE OF THE PEDAL GLANDS OF Damaliscus dorcas dorcas
Kovalev, B. G.,Sorochinskaya, A. M.,Avdeeva, L. A.
, p. 122 (1986)
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One-pot regio- and stereoselective cyclization of 1,2,n-triols
Zheng, Tao,Narayan, Radha S.,Schomaker, Jennifer M.,Borhan, Babak
, p. 6946 - 6947 (2007/10/03)
A simple and efficient process to cyclize triols containing a 1,2-diol functionality with a pendant hydroxyl group is presented. The one-pot procedure converts the 1,2-diol into an ortho ester in situ, which upon treatment with a Lewis acid generates a cyclic acetoxonium intermediate. This intermediate is subsequently trapped by the pendant hydroxyl group to generate a cyclic ether. The stereochemistry of the 1,2-diol is transferred to the product with complete fidelity (inversion at the site of cyclization), and the reaction proceeds with high regioselectivity. The process is akin to the Lewis acid-catalyzed intramolecular ring-opening of epoxides with hydroxyl groups yielding cyclic ethers of various sizes with regio- and stereochemical control. Copyright
Stereoselective alkenylation of activated olefins via nickel-catalyzed electroreductive coupling
Condon-Gueugnot, Sylvie,Dupre, Daniel,Nedelec, Jean-Yves,Perichon, Jacques
, p. 1457 - 1460 (2007/10/03)
The nickel-catalyzed electroreductive conjugate addition of (Z)- or (E)-alkyl halides to electron-deficient olefins in the presence of a sacrificial iron rod as the anode proceeds with complete retention of the stereochemistry of the alkenyl part and affo
