83665-87-6Relevant academic research and scientific papers
Substrate profile of an ω-transaminase from Burkholderia vietnamiensis and its potential for the production of optically pure amines and unnatural amino acids
Jiang, Jinju,Chen, Xi,Feng, Jinhui,Wu, Qiaqing,Zhu, Dunming
, p. 32 - 39 (2014/01/06)
A new (S)-enantioselective ω-transaminase (ω-TA) gene from Burkholderia vietnamiensis G4 was functionally expressed in Escherichia coli BL21 (DE3), and the purified recombinant N-terminal His-tagged ω-TA (HBV-ω-TA) had a dimeric structure with optimum pH and temperature of 8.4 and 40 C, respectively. The enzyme showed higher activities toward aromatic amines than aliphatic amines and (S)-1-methylbenzylamine ((S)-α-MBA) was the most active amino donor. For amino acceptor, keto acids, keto esters and aldehydes were more reactive than ketones with pyruvate ethyl ester being most active. Several chiral amines and unnatural amino acids or esters were synthesized using HBV-ω-TA as the catalyst and isopropylamine or (S)-α-MBA as amino donor. Notably, HBV-ω-TA catalyzed the amino transfer to β-keto esters to give optically pure β-amino acid esters. In addition, glyoxylate was used as amino acceptor for the first time in the kinetic resolution of racemic amines and optically pure amines, such as (R)-1-methylbenzylamine, (R)-1-phenylpropylamine, (R)-2-amino-4-phenylbutane and (R)-1-aminotetraline, were obtained.
Regioselective and stereospecific cross-coupling of primary allylic amines with boronic acids and boronates through palladium-catalyzed C-N bond cleavage
Li, Man-Bo,Wang, Yong,Tian, Shi-Kai
supporting information; experimental part, p. 2968 - 2971 (2012/04/18)
The NH2 group serves as an effective leaving group in the palladium-catalyzed regioselective and stereospecific title reaction (see scheme). The reaction works well with aryl- and alkenylboronic acids and aryl-, alkenyl-, allyl-, and benzylboronates, and complete transfer of chirality has been achieved when using α-chiral primary allylic amines as the allylic electrophiles. Copyright
Synthesis of the marine sponge alkaloid oroidin and its analogues via Suzuki cross-coupling reactions
Berrée, Fabienne,Girard-Le Bleis, Pascale,Carboni, Bertrand
, p. 4935 - 4938 (2007/10/03)
A new synthesis of the natural product oroidin was described using a Suzuki coupling reaction as key step. This method was extended to the synthesis of various analogues of oroidin and hymenidin.
Aminosilanes in organic synthesis. Hydrostannation of N,N-bis(trimethylsilyl)propargylamine. Facile and selective routes to (E)-allylic amines
Corriu, R.J.P.,Bolin, G.,Moreau, J.J.E.
, p. 273 - 280 (2007/10/02)
The addition of tributyl tin hydride to N,N-bis(trimethylsilyl)propargylamine yielded E-1-tributylstannyl-3-prop-1-ene 2 in 90percent yield and 96percent stereochemical purity.The functional vinyl tin reagent 2 was shown to give short and selective access to primary allylic amines.The reactions of 2 with aryl and vinyl bromides in the presence of a palladium catalyst gave substituted E-allylic amines in high yields.The reaction of 2 with butyl lithium yielded E-γ-vinyl lithium from which selective access to E-allylic amines was obtained.Key words: silylamines / propargylamines / hydrostannation / vinyl tin / vinyl lithium / (E)-allylamines
