- Development of an in situ-Product Crystallization (ISPC)-Concept to Shift the Reaction Equilibria of Selected Amine Transaminase-Catalyzed Reactions
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The synthesis of enantiopure amines via amine transaminases involves several challenges including unfavorable reaction equilibria and product inhibition. Described here is a non-catalytic approach to overcome such problems by using an in situ-product crystallization (ISPC) to selectively remove a targeted product amine from an amine transaminase-catalyzed reaction. The continuous removal of the product amine from its reaction solution as a barely soluble salt effectively yields a displacement of the reaction equilibrium towards the products and facilitates a simple downstream processing approach via filtration. The targeted product amine is eventually obtained from the salt, while the counterion compound can be easily recycled.
- Hülsewede, Dennis,T?nzler, Marco,Süss, Philipp,Mildner, Andrea,Menyes, Ulf,von Langermann, Jan
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p. 2130 - 2133
(2018/05/31)
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- Selective hydrogenation of arenes to cyclohexanes in water catalyzed by chitin-supported ruthenium nanoparticles
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The selective hydrogenation of aromatic compounds to cyclohexanes was found to be promoted by chitin-supported ruthenium nanoparticles (Ru/chitin) under near-neutral, aqueous conditions without the loss of C-O/C-N linkages at benzylic positions.
- Morioka, Yuna,Matsuoka, Aki,Binder, Kellie,Knappett, Benjamin R.,Wheatley, Andrew E.H.,Naka, Hiroshi
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p. 5801 - 5805
(2016/08/06)
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- Rhodium-catalyzed asymmetric hydrogenation of unprotected NH imines assisted by a thiourea
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Asymmetric hydrogenation of unprotected NH imines catalyzed by rhodium/bis(phosphine)-thiourea provided chiral amines with up to 97% yield and 95% ee. 1HNMR studies, coupled with control experiments, implied that catalytic chloride-bound intermediates were involved in the mechanism through a dual hydrogen-bonding interaction. Deuteration experiments proved that the hydrogenation proceeded through a pathway consistent with an imine.
- Zhao, Qingyang,Wen, Jialin,Tan, Renchang,Huang, Kexuan,Metola, Pedro,Wang, Rui,Anslyn, Eric V.,Zhang, Xumu
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supporting information
p. 8467 - 8470
(2014/08/18)
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- Enantioselective hydrogenation of N-H imines
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(Figure Presented) N-H ketoimines 3a-3v are readily prepared in high yield via organometallic addition to nitriles and isolated as corresponding bench-stable hydrochloride salts. Homogeneous asymmetric hydrogenation of unprotected N-H ketoimines 3a-3v usi
- Hou, Guohua,Gosselin, Francis,Li, Wei,McWilliams, J. Christopher,Sun, Yongkui,Weisel, Mark,O'Shea, Paul D.,Chen, Cheng-Yi,Davies, Ian W.,Zhang, Xumu
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supporting information; experimental part
p. 9882 - 9883
(2009/12/06)
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- Synthesis of enantiopure primary amines by stereoselective ring opening of chiral octahydro-1,3-benzoxazines by Grignard and organoaluminum reagents
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Chiral 1,3-perhydrobenzoxazines 1, 2, and 9-14, prepared by condensation of 8-(benzylamino)-menthol with different aldehydes, react with alkylmagnesium bromides and trimethylaluminum leading to the open amino alcohols 3a-d, 4a-d, and 15-20 in excellent chemical yields and good to excellent diastereomeric excess. The sequential elimination of the menthol appendage by heating with P2O5 and the benzyl group by hydrogenolysis lead to primary amines 7a-d, 8a-d, and 27-30 in excellent chemical yields and ee. The addition of the alkyl group from the Grignard derivatives and the methyl group from the trimethylaluminum occurs from opposite sides of the heterocycle, yielding the final primary amines with the same stereochemistry.
- Andrés, Celia,Nieto, Javier,Pedrosa, Rafael,Villama?án, Nieves
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p. 4130 - 4135
(2007/10/03)
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