119718-88-6Relevant academic research and scientific papers
Preparation of optically active cyanohydrins using the (S)-hydroxynitrile lyase from Hevea brasiliensis
Schmidt, Michael,Herve, Stephanie,Klempier, Norbert,Griengl, Herfried
, p. 7833 - 7840 (1996)
Several aliphatic, aromatic and heteroaromatic aldehydes have been converted into the chiral cyanohydrins using the (S) hydroxynitrile lyase from Hevea brasiliensis. The corresponding cyanohydrins were obtained in moderate to good yield and high enantiomeric excess with the exeption of phenyloxyacetaldehyde, benzyloxyacetaldehyde and the pyrrole-, pyridine- and indolealdehydes investigated. In contrast to previously reported results, cinnamaldehyde could be converted into (S)-(-)-2-hydroxy-4-phenyl-(E)-but-3- enenitrile with good selectivity by means of optimized reaction conditions.
On-step synthesis of a bifunctional BINOL ligand for the highly enantioselective cyanation of aliphatic aldehydes
Qin, Ying-Chuan,Liu, Lan,Pu, Lin
, p. 2381 - 2383 (2005)
(Chemical Equation Presented) An efficient one-step synthesis of the optically active bifunctional BINOL ligand (S)-3 has been developed. It was found that (S)-3 in combination with Me2AlCl is a highly enantioselective catalyst for the addition of TMSCN to aliphatic aldehydes of diverse structures and is also among the most practical ones. A remarkable positive nonlinear effect was found for this chiral ligand.
Optimisation of the enantioselective synthesis of cyanohydrin esters
Veum, Lars,Kanerva, Liisa T.,Halling, Peter J.,Maschmeyer, Thomas,Hanefeld, Ulf
, p. 1015 - 1021 (2005)
The base- and lipase-catalysed enantioselective synthesis of cyanohydrin esters was investigated, and the problem of previously reported low yields due to residual water in the reaction mixture was addressed. When the lipase was immobilised on Celite R-633 as a carrier, both the enantioselectivity and the reaction times for this dynamic kinetic resolution were improved, thus enabling a highly enantioselective synthesis of aromatic and heteroaromatic cyanohydrin acetates.
Asymmetric synthesis of O-acetylcyanohydrins by reaction of aldehydes with NaCN/KCN catalyzed by recyclable chiral dimeric titanium(IV)/vanadium(V) salen complexes
Khan, Noor-Ul H.,Agrawal, Santosh,Kureshy, Rukhsana I.,Abdi, Sayed H. R.,Mayani, Vishal J.,Jasra, Raksh V.
, p. 3175 - 3180 (2006)
The efficient catalytic asymmetric addition of an inexpensive and nonvolatile cyanide source such as NaCN or KCN and acetic anhydride to various aldehydes was catalyzed by recyclable dimeric TiIV and VV chiral salen complexes at -20°
A bimetallic aluminium(salen) complex for asymmetric cyanohydrin synthesis
North, Michael,Williamson, Courtney
, p. 3249 - 3252 (2009)
In the presence of a phosphine oxide cocatalyst, a bimetallic aluminium(salen) complex was found to catalyse the asymmetric addition of trimethylsilyl cyanide to aldehydes. Under optimised conditions, enantioselectivities of 53-96% were obtained using 2 m
An efficient titanium catalyst for enantioselective cyanation of aldehydes: Cooperative catalysis
Zhang, Zhipeng,Wang, Zheng,Zhang, Ruzhou,Ding, Kuiling
, p. 6746 - 6750 (2010)
(Figure Presented) Two-in-one: The integration of two salen/ Ti=O units into one molecule allows the enantioselective cyanation of aldehydes to afford the enantioenriched natural or nonnatural cyanohydrin derivatives with turnover numbers of 1960-172000 a
Catalytic, asymmetric synthesis of α-acetoxy amides
North, Michael,Parkins, Adrian W.,Shariff, Atiya N.
, p. 7625 - 7627 (2004)
Treatment of aldehydes with a titanium (salen) based catalyst, potassium cyanide and acetic anhydride gives non-racemic cyanohydrin acetates, which undergo chemoselective hydrolysis to α-acetoxy amides when treated with a platinum phosphinito catalyst.
Lipase-catalyzed dynamic kinetic resolution giving optically active cyanohydrins: use of silica-supported ammonium hydroxide and porous ceramic-immobilized lipase
Sakai, Takashi,Wang, Kefei,Ema, Tadashi
, p. 2178 - 2183 (2008)
Synthetically useful cyanohydrin acetates, ArCH(OAc)CN (Ar=C6H5, 3,4-methylenedioxyphenyl, 4-Me-C6H4, 4-Cl-C6H4, 4-F-C6H4, 4-CF3-C6H4), were successfully synthesized in high enantiomeric purities (79-93% ee) via the lipase-catalyzed dynamic kinetic resolution (DKR) of cyanohydrins synthesized in situ from the corresponding aldehydes and acetone cyanohydrin. The combined use of silica-supported BTAH (benzyltrimethylammonium hydroxide) and porous ceramic-immobilized lipase under the optimized reaction conditions enabled the remarkable acceleration of the enantioselective DKR reactions.
Direct and Post-Synthesis Incorporation of Chiral Metallosalen Catalysts into Metal-Organic Frameworks for Asymmetric Organic Transformations
Xi, Weiqin,Liu, Yan,Xia, Qingchun,Li, Zijian,Cui, Yong
, p. 12581 - 12585 (2015)
Two chiral porous metal-organic frameworks (MOFs) were constructed from [VO(salen)]-derived dicarboxylate and dipyridine bridging ligands. After oxidation of VIV to VV, they were found to be highly effective, recyclable, and reusable
Mechanistic comparison of aluminium based catalysts for asymmetric cyanohydrin synthesis
North, Michael,Villuendas, Pedro,Williamson, Courtney
, p. 1915 - 1924 (2010)
A kinetic analysis of the asymmetric addition of trimethylsilyl cyanide to benzaldehyde using three aluminium based catalysts has been carried out. All three catalysts displayed rate equations, which were first order in trimethylsilyl cyanide concentratio
