126641-87-0Relevant articles and documents
Lipase-catalyzed kinetic resolution with in situ racemization: One-pot synthesis of optically active cyanohydrin acetates from aldehydes
Inagaki, Minoru,Hiratake, Jun,Nishioka, Takaaki,Oda, JuN'Ichi
, p. 9360 - 9361 (1991)
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Synthesis of (1R,cis,αS)-cypermethrine via lipase catalyzed kinetic resolution of racemic m-phenoxybenzaldehyde cyanohydrin acetate
Roos, Juergen,Stelzer, Uwe,Effenberger, Franz
, p. 1043 - 1049 (1998)
A technical scale preparation of optically active (1R,cis, αS)- cypermethrine 4 from racemic m-phenoxybenzaldehyde cyanohydrin acetate (RS)- 1 and (1R,cis)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-carboxylic acid chloride (1R,cis)-3 is described. Key steps of the new procedure are a lipase catalyzed enantioselective transesterification of (RS)-1 with n-butanol and direct acylation of the mixture of (R)-1 and (S)-cyanohydrin (S)-2 with (1R,cis)-3 to give enantiomerically pure (1R,cis,αS)-4. The unchanged (R)-1 is removed from (1R,cis,αS)-4 by distillation, and is racemized with triethylamine to give (RS)-1 which is returned to the process. The total yield of (1R,cis,αS)-4 referred to (RS)-1 is 80%.
Fast microwave-assisted resolution of (±)-cyanohydrins promoted by lipase from Candida antarctica
Ribeiro, Sandra S.,Ferreira, Irlon M.,Lima, Jo?o P. F.,De Sousa, Bruno A.,Carmona, Rafaela C.,Santos, Alcindo A. Dos,Porto, André L. M.
, p. 1344 - 1350 (2015/07/15)
Enzymatic kinetic resolution (EKR) of (±)-cyanohydrins was performed by using immobilized lipase from Candida antarctica (CALB) under conventional ordinary conditions (orbital shaking) and under microwave radiation (MW). The use of microwave radiation contributed very expressively on the reduction of the reaction time from 24 to 2 h. Most importantly, high selectivity (up to 92percent eep) as well as conversion was achieved under MW radiation (50-56percent).
Asymmetric cyanosilylation of aldehydes catalyzed by novel organocatalysts
Wen, Yuehong,Huang, Xiao,Huang, Jinglun,Xiong, Yan,Qin, Bo,Feng, Xiaoming
, p. 2445 - 2448 (2007/10/03)
A novel proline-based N,N′-dioxide, which is easily prepared from inexpensive chemicals, serves as an effective catalyst for enantioselective cyanosilylation of aldehydes in up to 73% ee. Georg Thieme Verlag Stuttgart.
