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Chiral Molecular Tweezers: Synthesis and Reactivity in Asymmetric Hydrogenation

Lindqvist, M. and Borre, K. and Axenov, K. and Kótai, Bianka and Nieger, M. and Pápai, Imre (2015) Chiral Molecular Tweezers: Synthesis and Reactivity in Asymmetric Hydrogenation. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 137 (12). pp. 4038-4041. ISSN 0002-7863

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Abstract

We report the synthesis and reactivity of a chiral aminoborane displaying both rapid and reversible H-2 activation. The catalyst shows exceptional reactivity in asymmetric hydrogenation of enamines and unhindered imines with stereoselectivities of up to 99% ee. DFT analysis of the reaction mechanism pointed to the importance of both repulsive steric and stabilizing intermolecular non-covalent forces in the stereodetermining hydride transfer step of the catalytic cycle.

Item Type: Article
Uncontrolled Keywords: HYDROBORATION; BORANE; ENAMINES; ACTIVATION; IMINES; CORRESPONDING ALKENES; enantioselective hydrogenation; METAL-FREE HYDROGENATION; FREE CATALYTIC-HYDROGENATION; Frustrated lewis pairs
Subjects: Q Science / természettudomány > QD Chemistry / kémia
SWORD Depositor: MTMT SWORD
Depositing User: MTMT SWORD
Date Deposited: 24 Aug 2015 20:08
Last Modified: 01 Mar 2016 00:15
URI: http://real.mtak.hu/id/eprint/25961

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