459804-55-8

Upstream product

• 2935-35-5 (S)-2-phenylglycine 
• 20989-17-7 (2S)-2-phenylglycinol 
• 67-64-1 acetone 

Downstream Products

• 1448523-87-2 (Z)-N-(3-isopropyl-5-phenyl-1,3-selenazolidin-2-ylidene)-2-methoxybenzenamine 
• 929543-73-7 (2S)-1-isopropyl-2-phenylaziridine 

Relevant academic research and scientific papers

Enantioselective deprotometalation of alkyl ferrocenecarboxylates using bimetallic bases

The enantioselective deprotometalation of alkyl ferrocenecarboxylates (FcCO2R) using mixed lithium-zinc or lithium-cadmium bases is described. By using FcCO2Me as the substrate, chiral lithium alkyl-amidozincates prepared from exo-(αR)- or endo-(αS)-N-(α-phenylethyl)bornylamine (H-exo-born-R or H-endo-born-S) were tested; the best results (27% yield and 62% ee in favor of the RP enantiomer) were obtained by using Bu2(endo-born-S)ZnLi in tetrahydrofuran (THF) at -30 °C before iodolysis. Due to the low compatibility of FcCO2Me with alkyl-containing lithium zincates, 1?:?1 mixtures of lithium and zinc amides were tested. Chiral (H-exo-born-R or H-endo-born-S) or/and achiral (lithium 2,2,6,6-tetramethylpiperidide or lithium diisopropylamide) secondary amines gave good results, the best (81% yield and 44% ee in favor of the RP enantiomer) being obtained by using (endo-born-S)3ZnLi in THF at room temperature. Among other secondary amines also prepared and/or tested, commercial (S,S)-bis(α-phenylethyl)amine (H-PEA-S) proved promising. After optimization of the reaction conditions, the best enantioselectivity (26% yield and 80% ee in favor of the RP enantiomer) was observed by treating a THF solution of FcCO2Me and Zn(PEA-S)2 with Li-PEA-S at -80 °C before iodolysis. That no reaction took place with cadmium instead of zinc suggests the formation of 'ate complexes upon treatment of Cd(PEA-S)2 by Li-PEA-S while Zn(PEA-S)2 and Li-PEA-S would rather work in tandem (Li-PEA-S as the base and Zn(PEA-S)2 as the in situ trap for the formed ferrocenyllithium). While FcCO2Me, FcCO2tBu and FcCO2iPr could be converted into their racemic 2-iodinated derivatives with a yield of 84 to 87% by employing LiTMP (2 equiv.) in the presence of ZnCl2·TMEDA (1 equiv.) as an in situ trap, their enantioselective deprotometalation rather required Li-PEA-S together with Zn(PEA-S)2 to produce the enantio-enriched derivatives with yields of 45-82% and 71% ee. This journal is

"On water": Efficient iron-catalyzed cycloaddition of aziridines with heterocumulenes

In suspension: The reaction of aziridines with heterocumulenes in the presence of Fe(NO3)3×9 H2O in aqueous suspension provides access to functionalized five-membered heterocycles in good to high yields. This protocol has a wide substrate scope, is simple, and uses a nontoxic and cheap catalyst. Copyright

Preparation of phenolic chiral crown ethers and podands and their enantiomer recognition ability toward secondary amines

Phenolic pseudo-24-crown-8 (S,S)-3, pseudo-27-crown-9 (S,S)-4, and podands (R,R)-5 and (R,R)-6 possessing phenyl groups as chiral barriers were prepared and their chiral recognition properties toward secondary neutral amines were examined. Pseudo-24-crown-8 (S,S)-3 and podand (R,R)-5 showed sufficient binding ability and moderate chiral recognition ability toward secondary amines.

Asymmetric addition of n-butyllithium to aldehydes: New insights into the reactivity and enantioselectivity of the chiral amino ether accelerated reaction

Enantioselective butylation of benzaldehyde with n-butyllithium was mediated by a series of chiral lithium amide analogues to give 1-phenylpentanol in good to moderate enantioselectivities. In order to achieve high enantiomeric excess in the reaction, the lithium amide must have a substituent larger than methyl on both the carbon at the stereogenic center and the nitrogen. Computational studies, using semi-empirical (PM3) and density functional (B3LYP) methods, show that the stabilities of the transition states for the chiral lithium amide accelerated butylation of isobutyraldehyde are in agreement with experiments.