59562-82-2Relevant articles and documents
An Amphiphilic (salen)Co Complex – Utilizing Hydrophobic Interactions to Enhance the Efficiency of a Cooperative Catalyst
Solís-Mu?ana, Pablo,Salam, Joanne,Ren, Chloe Z.-J.,Carr, Bronte,Whitten, Andrew E.,Warr, Gregory G.,Chen, Jack L.-Y.
supporting information, p. 3207 - 3213 (2021/06/01)
An amphiphilic (salen)Co(III) complex is presented that accelerates the hydrolytic kinetic resolution (HKR) of epoxides almost 10 times faster than catalysts from commercially available sources. This was achieved by introducing hydrophobic chains that increase the rate of reaction in one of two ways – by enhancing cooperativity under homogeneous conditions, and increasing the interfacial area under biphasic reaction conditions. While numerous strategies have been employed to increase the efficiency of cooperative catalysts, the utilization of hydrophobic interactions is scarce. With the recent upsurge in green chemistry methods that conduct reactions ‘on water’ and at the oil-water interface, the introduction of hydrophobic interactions has potential to become a general strategy for enhancing the catalytic efficiency of cooperative catalytic systems. (Figure presented.).
Catalytic Diastereo- and Enantioconvergent Synthesis of Vicinal Diamines from Diols through Borrowing Hydrogen
Feng, Wei,Gao, Taotao,Lau, Kai Kiat,Lin, Yamei,Pan, Hui-Jie,Yang, Binmiao,Zhao, Yu
supporting information, p. 18599 - 18604 (2021/08/09)
We present herein an unprecedented diastereoconvergent synthesis of vicinal diamines from diols through an economical, redox-neutral process. Under cooperative ruthenium and Lewis acid catalysis, readily available anilines and 1,2-diols (as a mixture of diastereomers) couple to forge two C?N bonds in an efficient and diastereoselective fashion. By identifying an effective chiral iridium/phosphoric acid co-catalyzed procedure, the first enantioconvergent double amination of racemic 1,2-diols has also been achieved, resulting in a practical access to highly valuable enantioenriched vicinal diamines.
One-Pot Three-Step Consecutive Transformation of L-α-Amino Acids to (R)- and (S)-Vicinal 1,2-Diols via Combined Chemical and Biocatalytic Process
Zhang, Jian-Dong,Zhao, Jian-Wei,Gao, Li-Li,Zhao, Jing,Chang, Hong-Hong,Wei, Wen-Long
, p. 5032 - 5037 (2019/10/28)
Optically pure vicinal 1,2-diols are versatile chiral building blocks in the fine chemical and pharmaceutical industries. L-α-amino acid is a good feedstock source for high value-added product production since it is inexpensive and renewable. However, conversion of L-α-amino acids to enantioenriched vicinal 1,2-diols remains a significant challenge. In this study, combining a simple chemical process and a three-enzyme cascade biocatalysis system, we have successfully implemented a one-pot sequential process for the transformation of L-α-amino acids into enantiopure vicinal 1,2-diols in aqueous medium. Firstly, the NaBH4-H2SO4 system converted L-α-amino acids to (S)-amino alcohols via amino acid carboxyl reduction. Secondly, the three-enzyme (transaminase, carbonyl reductase and glucose dehydrogenase) cascade biocatalysis system converted amino alcohols to enantiopure vicinal 1,2-diols via amino alcohol deamination, α-hydroxy ketone asymmetric reduction and cofactor regeneration. Taking advantage of the two different reaction systems, chiral vicinal 1,2-diols could be obtained from L-α-amino acids with high yields (69–90 %) and excellent ee values (91–>99 % ee).
