36940-65-5Relevant academic research and scientific papers
A Single Lipase-Catalysed One-Pot Protocol Combining Aminolysis Resolution and Aza-Michael Addition: An Easy and Efficient Way to Synthesise β-Amino Acid Esters
Xu, Fan,Wu, Qiongsi,Chen, Xiaoyang,Lin, Xianfu,Wu, Qi
, p. 5393 - 5401 (2015/08/24)
A novel one-pot protocol combining aza-Michael addition and aminolysis resolution was developed to obtain chiral β-amino acid esters with lipase B from Candida antarctica (CAL-B) as the only catalyst. This method is conducted under mild reaction conditions and is very easy to handle. After a series of detailed optimization studies, ten racemic aromatic or aliphatic amines were subjected to this one-pot procedure, and twelve chiral β-amino acid esters and ten chiral amides were successfully synthesised with excellent ee values in theoretical yields. Scaled-up procedures also worked without apparent reduction in reaction rate or enantioselectivity, which makes this method suitable for large-scale production of chiral β-amino acid esters. A one-pot protocol for simultaneous synthesis of chiral β-amino acid esters and amides was developed by combining single lipase B from Candida antarctica (CAL-B) catalysed aza-Michael addition and aminolysis resolution. This method requires mild reaction conditions and is very easy to handle. Chiral β-amino acid esters and chiral amides were obtained with excellent ee values and in theoretical yields.
Thiyl radical mediated racemization of benzylic amines
Escoubet, Stephanie,Gastaldi, Stephane,Vanthuyne, Nicolas,Gil, Gerard,Siri, Didier,Bertrand, Michele P.
, p. 3242 - 3250 (2007/10/03)
Thiyl radical mediated reversible H abstraction from the stereogenic center α to the nitrogen atom is a mild method to racemize benzylic amines. Owing to the sensitivity of atomtransfer reactions to enthalpic effects, a knowledge of both the S-H and the α-C-H bond dissociation energies is fundamental to select the thiol that is appropriate to abstract the hydrogen atom from a given amine. In the absence of experimental data, theoretical calculations supply a useful predictive tool. The experiments described here are helpful in delineating the optimal conditions that have to be fulfilled for the racemization to proceed in a reasonable time in the presence of either a stoichiometric or a catalytic amount of thiol. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Stereospecific synthesis of tetradeuterated (R)- and (S)-ifosfamide
Wang,Chan
, p. 105 - 115 (2007/10/03)
The tetradeuterated analogues of (R)- and (S)-ifosfamide [(S)- and (R)-2-(2-chloro-2,2-dideuterioethyl)amino-3-(2-chloroethyl)-6,6-dideuterio -tetrahydro-2H-1,3,2-oxazaphosphorin-2-oxide, (S)- and (R)-1-d4] were synthesized by modification of a
