503188-04-3Relevant academic research and scientific papers
Efficient Lipase-Catalyzed Kinetic Resolution and Dynamic Kinetic Resolution of β-Hydroxy Nitriles. Correction of Absolute Configuration and Transformation to Chiral β-Hydroxy Acids and γ-Amino Alcohols
Pamies, Oscar,Baeckvall, Jan-E.
, p. 947 - 952 (2002)
Chemoenzymatic dynamic kinetic resolution of β-hydroxy nitriles 1 has been carried out using Candida antarctica lipase B and a ruthenium catalyst. The use of a hydrogen source to depress ketone formation in the dynamic kinetic resolution yields the corresponding acetates 2 in good yield and high enantioselectivity. It is shown that the ruthenium catalyst and the enzyme can be recycled when used in separate reactions. We also report on the preparation of various enantiomerically pure β-hydroxy acid derivatives and γ-amino alcohols from 1 and 2. The latter compounds were also used to establish the correct absolute configuration of 1 and 2.
Ni(II)-Catalyzed Enantioselective Synthesis of β-Hydroxy Esters with Carboxylate Assistance
Wang, Na,Liu, Hongxin,Gao, Hang,Zhou, Jiafeng,Zheng, Longzhangdi,Li, Juan,Xiao, Hong-Ping,Li, Xinhua,Jiang, Jun
supporting information, p. 6684 - 6689 (2019/08/26)
A Ni-oxazoline complex-catalyzed asymmetric decarboxylative aldol reaction between malonic acid half-oxyesters and various carbonyls with carboxylate assistance was developed, affording structurally diverse β-hydroxy esters with good yields and enantioselectivities under mild conditions. Importantly, the broad substrate scope of this methodology enabled rapid accesses to several natural products and their analogues as exemplified by phenylpropanoid, phaitanthrin B, and phthalide.
Asymmetric synthesis of both antipodes of β-hydroxy nitriles and β-Hydroxy carboxylic acids via enzymatic reduction or sequential reduction/hydrolysis
Ankati, Haribabu,Zhu, Dunming,Yang, Yan,Biehl, Edward R.,Hua, Ling
supporting information; experimental part, p. 1658 - 1662 (2009/08/08)
Use of isolated carbonyl reductases in the reduction of aromatic β-ketonitriles have completely eliminated the competing α-ethylation, which is often observed with whole cell biocatalysts. By choosing suitable recombinant carbonyl reductase, the reduction
