1026730-55-1Relevant articles and documents
Efficient Asymmetric Biomimetic Aldol Reaction of Glycinates and Trifluoromethyl Ketones by Carbonyl Catalysis
Cao, Jing,Cheng, Aolin,Liu, Tao,Song, Guanshui,Zhang, Kun,Zhang, Liangliang,Zhao, Baoguo,Zhao, Guoqing,Zhou, Qinghai
supporting information, p. 20166 - 20172 (2021/07/20)
The direct asymmetric aldol reaction of glycinates represents an intriguing and straightforward strategy to make biologically significant chiral β-hydroxy-α-amino-acid derivatives. But it is not easy to realize the transformation due to the disruption of the reactive NH2 group of glycinates. Inspired by the enzymatic aldol reaction of glycine, we successfully developed an asymmetric aldol reaction of glycinate 5 and trifluoromethyl ketones 4 with 0.1–0.0033 mol % of chiral N-methyl pyridoxal 7 a as the catalyst, producing chiral β-trifluoromethyl-β-hydroxy-α-amino-acid esters 6 in 55–82 % yields (for the syn-diastereomers) with up to >20:1 dr and 99 % ee under very mild conditions. The reaction proceeds via a catalytic cycle similar to the enzymatic aldol reaction of glycine. Pyridoxal catalyst 7 a activates both reactants at the same time and brings them together in a specific spatial orientation, accounting for the high efficiency as well as excellent diastereo- and enantioselectivities.
Efficient synthesis of optically pure 1,1,1-trifluoro-2-alkanols through lipase-catalyzed acylation in organic media
Hamada, Hiroki,Shiromoto, Mizuho,Funahashi, Makoto,Itoh, Toshiyuki,Nakamura, Kaoru
, p. 2332 - 2336 (2007/10/03)
Lipase-catalyzed esterification was successfully utilized for the optical resolution of 1,1,1-trifluoro-2-alkanol 1 when racemic 1 was treated with lipase from Candida antarctica in hexane in the presence of molecular sieves (4 A) to provide the corresponding (S)-acetate 2 in an optically pure state. Alkanol 1 is known as an important component of liquid crystal compounds which display remarkable ferroelectric liquid crystal (FLC) characteristics. Five types of optically pure alkanols, i.e., 1,1,1-trifluoro-2-octanol (1a), 1,1,1-trifluoro-2-nonanol (1b), 1,1,1-trifluoro-2-decanol (1c), 1,1,1-trifluoro-2-undecanol (1d), and 1,1,1-trifluoro-8-(benzyloxy)-2-octanol (1e), were thus obtained by the lipase-catalyzed acylation.