134477-75-1Relevant academic research and scientific papers
Chiral primary amine catalyzed asymmetric epoxidation of α-substituted acroleins
Li, Jiuyuan,Fu, Niankai,Zhang, Long,Zhou, Pengxin,Luo, Sanzhong,Cheng, Jin-Pei
supporting information; experimental part, p. 6840 - 6849 (2011/03/19)
1,1-Disubstituted terminal alkenes remain challenging substrates in asymmetric epoxidation reactions. In this study, chiral primary amines are shown to catalyze the asymmetric epoxidation of α-substituted acroleins, a versatile type of 1,1-disubstituted t
Rapid organocatalytic aldehyde-aldehyde condensation reactions
Erkkilae, Anniina,Pihko, Petri M.
, p. 4205 - 4216 (2008/03/14)
We report the results of the systematic optimization of the α-methylenation of aldehydes with aqueous formaldehyde. A simple combination of a secondary amine catalyst and a weak acid co-catalyst has been identified, allowing access to α-substituted acroleins in a matter of minutes. In the absence of formaldehyde, the catalytic system promoted the self-condensation reaction of α,β-unsaturated aldehydes. Both of these reactions exhibited linear relationships between co-catalyst acidities and reaction rates. A second-order dependence of catalyst concentration was observed, pointing to the involvement of two molecules of the ammonium catalyst in the rate-determining step. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Mild organocatalytic α-methylenation of aldehydes
Erkkil?, Anniina,Pihko, Petri M.
, p. 2538 - 2541 (2007/10/03)
A rapid and extremely convenient method for α-methylenation of aldehydes with aqueous formaldehyde is described. Two optimal catalytic systems are presented that allow short reaction times and afford the functionalized products in good to excellent yields (up to 99%) and chemoselectivity.
Transformation of esters into 2-substituted allyl halides via tertiary cyclopropanols: Application in the stereoselective synthesis of (2S,3S,7S)-3,7-dimethyl-2-pentadecyl acetate, the sex pheromone of the pine sawfly Neodiprion sertifer
Bekish, Andrei V.,Prokhorevich, Konstantin N.,Kulinkovich, Oleg G.
, p. 5069 - 5075 (2007/10/03)
(2S,3S,7S)-3,7-Dimethyl-2-pentadecyl acetate (ac-1), the sex pheromone of the pine sawfly Neodiprion sertifer, has been newly synthesized by the transformation of the corresponding esters 8 and 12 into 2-oxyalkyl-substituted allyl bromides 4 and 5 via ter
Baker's yeast mediated biohydrogenation of unsaturated compounds containing a methylene group: Enantioselective preparation of 2-methyl alkanols from 2-substituted acrolein acetals
Ferraboschi, Patrizia,Reza-Elahi, Shahrzad,Verza, Elisa,Santaniello, Enzo
, p. 2639 - 2642 (2007/10/03)
The baker's yeast mediated biohydrogenation of unsaturated compounds containing a methylene group may constitute an enantioselective biocatalytic approach to the preparation of 2-methyl-1-alkanols, as exemplified by the reduction of the compounds 8a-d to 90-98% enantiomerically pure alcohols 2a-d.
