105590-48-5Relevant academic research and scientific papers
TBD/Al2O3: A novel catalytic system for dynamic intermolecular aldol reactions that exhibit complex system behaviour
Martinez-Castaneda, Angel,Rodriguez-Solla, Humberto,Concellon, Carmen,Del Amo, Vicente
, p. 1976 - 1981 (2012)
The heterogeneous system TBD/Al2O3 is an efficient catalyst for the intermolecular aldol reaction between ketones and aromatic aldehydes. This system operates with low catalysts loading (10%), in water or organic solvents, and with s
Direct organocatalytic aldol reactions in buffered aqueous media
Cordova, Armando,Notz, Wolfgang,Barbas III, Carlos F.
, p. 3024 - 3025 (2002)
Organocatalytic cross-aldol reactions catalyzed by cyclic secondary amines in aqueous media provide a direct route to a variety of aldols including carbohydrate derivatives and may warrant consideration as a prebiotic route to sugars.
A comprehensive study on the effect of acid additives in 1( R),2( R)-Bis[(S)-prolinamido]cyclohexane catalyzed direct asymmetric aldol reactions in aqueous media
Bhowmick, Sudipto,Kunte, Sunita S.,Bhowmick, Kartick C.
, p. 84 - 92 (2015/01/30)
The catalytic efficacy of (1R,2 R)-bis[(S)-prolinamido]cyclohexane 1, prepared from the readily available natural amino acid L-proline has been studied for the direct asymmetric aldol reaction of cyclohexanone with substituted benzaldehydes at room temper
Highly enantioselective aldol reactions using a tropos dibenz[c,e]azepine organocatalyst
Lygo, Barry,Davison, Christopher,Evans, Timothy,Gilks, James A.R.,Leonard, John,Roy, Claude-Eric
supporting information; experimental part, p. 10164 - 10170 (2012/01/03)
The four-step synthesis of a chiral primary tertiary diamine salt, possessing a tropos dibenz[c,e]azepine ring is described. It is shown that 3.5-5 mol % of this salt is capable of promoting highly enantioselective crossed-aldol reactions between cyclohexanone and a series of aromatic aldehydes. In all cases, the aldol reactions proceed with high diastereoselectivity for the anti-aldol product. The outcome of crossed-aldol reactions involving other cyclic ketones and acyclic ketones are also described. All examples involving cyclic ketones result in selectivity for the anti-aldol products, whereas acyclic ketones were found to favour the syn-aldol products. A discussion on the role of the chiral primary tertiary diamine salt in the catalysis of the aldol reactions is also presented.
Highly efficient primary amine organocatalysts for the direct asymmetric aldol reaction in brine
Ma, Xiao,Da, Chao-Shan,Yi, Lei,Jia, Ya-Ning,Guo, Qi-Peng,Che, Li-Ping,Wu, Feng-Chun,Wang, Jun-Rui,Li, Wei-Ping
experimental part, p. 1419 - 1424 (2009/12/04)
Organocatalytic systems made up of six primary amine organocatalysts, derived from natural primary amino acids, in combination with 2,4-dinitrophenol (DNP) have proven to be efficient in the presence of brine without further addition of organic solvents. The system formed by 1f and DNP was the most efficient one; it can catalyze the direct aldol reaction with a broad range of ketones and aromatic aldehydes, giving the corresponding aldol products in high yields with up to nearly perfect diastereo- and enantioselectivities (up to 99/1 syn/anti, >99% ee).
Protonated (S)-prolinamide derivatives-water compatible organocatalysts for direct asymmetric aldol reaction
Singh Chimni, Swapandeep,Singh, Sarbjit,Mahajan, Dinesh
experimental part, p. 2276 - 2284 (2009/04/11)
Protonated chiral (S)-prolinamide derivatives have been developed as water compatible highly efficient organocatalysts for a direct enantioselective aldol reaction. A simple protonated (S)-prolinamide organocatalyst prepared from l-proline and 3-nitroanil
A NOVEL NUCLEOPHILIC SUBSTITUTION OF THE FORMYL GROUP IN p-NITROBENZALDEHYDE WITH SOME CARBANIONS
Iwasaki, Genji,Saeki, Seitaro,Hamana, Masatomo
, p. 173 - 176 (2007/10/02)
p-Nitrobenzaldehyde reacts with some active methylene compounds in the presence of a strong base at low temperatures to give p-substituted nitrobenzenes by the two-step course involving the initial formation of the aldol adducts and the subsequent displacement of the carbinol moieties with excess carbanions.
