830-02-4Relevant articles and documents
Copper-Catalyzed Stereoselective Defluorinative Borylation and Silylation of gem-Difluoroalkenes
Tan, Dong-Hang,Lin,Ji, Wei-Wei,Zeng, Yao-Fu,Fan, Wen-Xin,Li, Qingjiang,Gao, Hui,Wang, Honggen
, p. 1032 - 1037 (2018)
The copper-catalyzed stereoselective defluorinative borylation and silylation of gem-difluoroalkenes was developed. The protocol led to the exclusive formation of Z type monofluoroalkenyl borons and silanes in generally good efficiency with broad substrat
Asymmetric Synthesis of Alkyl Fluorides: Hydrogenation of Fluorinated Olefins
Ponra, Sudipta,Yang, Jianping,Kerdphon, Sutthichat,Andersson, Pher G.
supporting information, p. 9282 - 9287 (2019/05/28)
The development of new general methods for the synthesis of chiral fluorine-containing molecules is important for several scientific disciplines. We herein disclose a straightforward method for the preparation of chiral organofluorine molecules that is ba
One-Pot l-Proline-Mediated Stereoselective α-C(sp2)–H Fluorination of α,β-Unsaturated Aldehydes through Methoxyfluorination–Elimination
Zhou, Jiadi,Jiang, Xinpeng,Jin, Can,Guo, Zhicheng,Su, Bin,Su, Weike
, p. 3631 - 3634 (2017/07/22)
A one-pot, two-step l-proline-mediated stereoselective α-C(sp2)–H fluorination of α,β-unsaturated aldehydes towards their corresponding (Z)-α-fluoro-α,β-unsaturated aldehydes has been developed. The first step utilises Selectfluor as a fluorinating agent in CH3NO2/MeOH forming (Z)-α-fluoro-α,β-unsaturated aldehydes and their corresponding dimethyl acetals through methoxyfluorination-elimination. In the second step, water is added to promote the hydrolytic cleavage of the dimethyl acetals. The obtained (Z)-α-fluoro-α,β-unsaturated aldehydes were smoothly reduced to the corresponding alcohols by using NaBH4.
Highly regioselective SN2′ reaction of β-fluoroallylic phosphates with organocopper reagents and its application to the synthesis of fluorine-containing carbocycles
Nihei, Takashi,Kubo, Yusuke,Ishihara, Takashi,Konno, Tsutomu
, p. 110 - 121 (2015/03/04)
Treatment of β-fluoroallyl phosphates with 2.2 equiv. of organocuprates, prepared readily from 2.2 equiv. each of CuCN and organometallics (organolithium reagents, Grignard reagents, and organozinc reagents), in THF at -40 to 0 °C for 0.25 to 24 h gave γ-products in a highly regioselective manner. Thus obtained γ-adducts were subjected to the ring-closing metathesis, the corresponding cyclic fluoroalkenes being afforded in good yields.
Efficient access to fluorinated homoallylic alcohols through an indium promoted fluoroallylation reaction
Lemonnier, Gérald,Van Hijfte, Nathalie,Sebban, Muriel,Poisson, Thomas,Couve-Bonnaire, Samuel,Pannecoucke, Xavier
, p. 3123 - 3133 (2014/05/06)
Herein, an efficient access to fluorinated homoallylic alcohol is reported. The fluorinated alcohols were obtained in good to excellent yield using indium and halo-fluorinated allylic derivatives. The developed methodology using γ-substituted halo-fluorin
Enantioselective bioreduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae
Luo, Fan,Lu, Dengfu,Gong, Yuefa
experimental part, p. 101 - 107 (2012/02/04)
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.
Synthesis of fluorinated pseudopeptides: Metal mediated reversal of stereochemistry in diastereoselective addition of organometallic reagents to N-(tert-butanesulfinyl)-α-fluoroenimines
Pierry, Camille,Cahard, Dominique,Couve-Bonnaire, Samuel,Pannecoucke, Xavier
experimental part, p. 2378 - 2386 (2011/05/14)
The addition reaction of organometallic reagents to N-(tert-butanesulfinyl) -α-fluoroenimines was studied. Depending of the nature of the organometallic species (Grignard reagents or zincate complexes), we were able to control the configuration of the new
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.
A new route for the synthesis of mono-flourinated allyl alcohols using the stereoselective Wittig olefination via reaction of (α-flurovinyl)triphenylphosphonium triflate
Hanamoto,Nishiyama,Tateishi,Kondo
, p. 1320 - 1322 (2007/10/03)
The three-component coupling reaction of (α-fluorovinyl)triphenylphosphonium triflate, cesium allylate, and aldehydes in trimethyl orthoformate gave the corresponding mono-fluorinated allyl ethers with good stereoselectivity; the resulting ethers were readily transformed into the corresponding mono-fluorinated allyl alcohols using the Cp2Zr-mediated reaction.
