1221508-36-6Relevant articles and documents
Enantioselective bioreduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae
Luo, Fan,Lu, Dengfu,Gong, Yuefa
, p. 101 - 107 (2011)
Biocatalytic reduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae underwent smoothly and yielded (S)-2-fluorinated alkanols with high enantioselectivities. The conversion rate was markedly depending on the configuration of alkene moiety of the substrate, the chain length of alkyl group at β position of CC bond, as well as the reaction conditions.
Enantio- and Diastereoselective Hydrofluorination of Enals by N-Heterocyclic Carbene Catalysis
Wang, Leming,Jiang, Xinhang,Chen, Jiean,Huang, Yong
, p. 7410 - 7414 (2019)
In contrast to well-established asymmetric hydrogenation reactions, enantioselective protonation is an orthogonal approach for creating highly valuable methine chiral centers under redox-neutral conditions. Reported here is the highly enantio- and diastereoselective hydrofluorination of enals by an asymmetric β-protonation/α-fluorination cascade catalyzed by N-heterocyclic carbenes (NHCs). The two nucleophilic sites of a homoenolate intermediate, generated from enals and an NHC, are sequentially protonated and fluorinated. The results show that controlling the relative rates of protonation, fluorination, and esterification is crucial for this transformation, and can be accomplished using a dual shuttling strategy. Structurally diverse carboxylic acid derivatives with two contiguous chiral centers are prepared in a single step with excellent d.r. and ee values.
Asymmetric synthesis of 1,2-fluorohydrin: Iridium catalyzed hydrogenation of fluorinated allylic alcohol
Ponra, Sudipta,Yang, Jianping,Wu, Haibo,Rabten, Wangchuk,Andersson, Pher G.
, p. 11189 - 11194 (2020/11/04)
We have developed a simple protocol for the preparation of 1,2-fluorohydrin by asymmetric hydrogenation of fluorinated allylic alcohols using an efficient azabicyclo thiazole-phosphine iridium complex. The iridium-catalyzed asymmetric synthesis of chiral 1,2-fluorohydrin molecules was carried out at ambient temperature with operational simplicity, and scalability. This method was compatible with various aromatic, aliphatic, and heterocyclic fluorinated compounds as well as a variety of polyfluorinated compounds, providing the corresponding products in excellent yields and enantioselectivities. This journal is
Highly enantioselective bioreduction of 2-fluorocinnamyl alcohols mediated by Saccharomyces cerevisiae
Luo, Fan,Wang, Ping,Gong, Yuefa
supporting information; experimental part, p. 1693 - 1695 (2010/04/29)
Biocatalytic reduction of 2-fluorocinnamyl alcohols mediated by Saccharomyces cerevisiae was investigated in phosphate buffer solutions. Product analysis clearly showed that (S)-2-fluoro-3-arylpropanols were afforded in high yields with up to 92% ee value.