91373-64-7

Upstream product

• 3182-95-4 L-Phenylalaninol 
• 67-64-1 acetone 
• 63-91-2 L-phenylalanine 
• 90600-04-7 N-isopropyl-L-phenylalanine 

Downstream Products

• 91373-88-5 (S)-2-Isopropylamino-3-phenyl-propan-1-ol; compound with (S)-3-acetylsulfanyl-2-methyl-propionic acid 

Relevant academic research and scientific papers

Synthesis and application of oxadiazines as chiral ligands for the enantioselective addition of diethylzinc to aldehydes

A series of oxadiazines derived from l-phenylalanine bearing phenolic substituents have been synthesized in a multistep, one pot process. This process involves the reaction of a mixed anhydride with a β-hydrazino alcohol, methanesulfonylation of the alcohol moiety, and base induced cyclization. The resultant oxadiazines were employed in the asymmetric addition of diethylzinc to aldehydes.

Synthesis, reactivity and conformational stability of an l-phenylalanine derived oxadiazinanone

An l-phenylalanine derived oxadiazinanone bearing an isopropyl group at the N4-position was prepared and acylated with either hydrocinnamoyl or propanoyl chloride. These oxadiazinanones were utilized in titanium-mediated asymmetric aldol reacti

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.

An Improved Optical Resolution of 3-Acetylthio-2-methylpropionic Acid by Use of a New Chiral Amine, N-Isopropyl(phenylalaninol)

(S)-3-Acetylthio-2-methylpropionic acid was obtained in a good yield by an effective optical resolution with a newly synthesized chiral amine, (S)-N-isopropyl(phenylalaninol), which was readily derived from (S)-phenylalaninol, as a resolving agent.Keyword

ENANTIOSELECTIVE SYNTHESIS OF β-HYDROXY-α-METHYL CARBONYL COMPOUNDS BY ALDOL REACTION

The enantioselective aldol reactions of ketone lithium enolates with aldehydes mediated chiral lithium amides were extensively investigated.The chiral amino ethers 4a-4l and diamines 16a,b were prepared from α-amino acids.The reaction conditions and the s

Optically active N-substituted phenylalaninols and use thereof

Optically active N-substituted phenylalaninols of the formula (I): STR1 wherein R is isopropyl, 1-ethylpropyl, cyclopentyl, cyclohexyl, cycloheptyl, 4-methylbenzyl, 4-methoxybenzyl, or 3,4-methylenedioxybenzyl; and acid addition salts thereof which are useful as a resolving agent, and a process for preparing D-3-acetylthio-2-methylpropionic acid which comprises reacting DL-3-acetylthio-2-methylpropionic acid with an optically active N-substituted phenylalaninol of the formula (I) to form diastereomeric salts, subjecting the formed diastereomeric salts to a fractional crystallization from a solvent to separate the D-acid salt from the L-acid salt, and then decomposing the D-acid salt with a mineral acid to give D-3-acetylthio-2-methylpropionic acid.