116126-04-6Relevant articles and documents
Enantiomerically pure N-Boc- and N-benzoyl-(S)-phenylglycinals
Wroblewski, Andrzej E.,Piotrowska, Dorota G.
, p. 2509 - 2512 (2002)
Enantiomerically pure N-Boc- and N-benzoyl-(S)-phenylglycinals were prepared by oxidation of the respective alcohols with Dess-Martin periodinane. The glycinals were phosphonylated with lithium O,O-dimethyl phosphonate at -70°C or (MeO)2POTMS a
Direct asymmetric reductive amination of α-keto acetals: A platform for synthesizing diverse α-functionalized amines
Chiu, Pauline,Shi, Yongjie,Wang, Chenhan,Wang, Jingxin,Yang, Feifan,Yin, Qin,Zhang, Xumu
, p. 513 - 516 (2022/01/22)
We report an efficient and straightforward method to synthesize enantio-enriched N-unprotected α-amino acetals via ruthenium-catalyzed direct asymmetric reductive amination. The α-amino acetal products are versatile and valuable platform molecules that can be converted to the corresponding α-amino acids, amino alcohols, and other derivatives by convenient transformations.
Iron/caffeine as a catalytic system for microwave-promoted benzamide formation
Bantreil, Xavier,Navals, Pauline,Martinez, Jean,Lamaty, Fr??d??ric
, p. 417 - 422 (2015/03/03)
The amide bond is an essential unit in many drugs and polymers. The catalyzed oxidation of alcohols and amines is an effective method to form amides with limited undesired waste. Herein, we demonstrate the beneficial effect of microwave activation for this reaction. The benzamides were directly formed from alcohols and amine hydrochloride salts in short reaction times with yields up to 84% and TOFs (turnover frequencies) up to 33.6 h-1. Among the examined transition metals, only nontoxic and inexpensive FeCl2?·4H2O together with caffeine as a stabilizing ligand provided a uniquely efficient catalytic system for the transformation. Natural sources of caffeine were also evaluated under the amidation conditions.
Simple methodology for the preparation of amino alcohols from amino acid esters using nabh4-methanol in THF
Goncalves,Pinheiro,Da Silva,Da Costa,Kaiser,De Souza
experimental part, p. 1276 - 1281 (2011/05/04)
Amino alcohols constitute a very useful and versatile class of organic compounds, with important applications in synthetic and medicinal chemistry. However, in most of the procedures described in the literature for the obtainment of these compounds, considerable limitations can be found, such as drastic conditions, long time reactions, poor yields, and purification problems. The present article describes a methodology that gives amino alcohols and N-protected amino alcohols based on the reduction of amino acid esters under mild conditions, employing NaBH4 in the presence of methanol. The reactions occurred in a short time (15-20min) and provide yields of 50-95%.