NDLI: Development of a Continuous-Flow System for Asymmetric Hydrogenation Using Self-Supported Chiral Catalysts

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Development of a Continuous-Flow System for Asymmetric Hydrogenation Using Self-Supported Chiral Catalysts

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Yu, Liting Wu, Jiang Sandoval, Christian A. Wang, Zheng Li, Hongji Shi, Lei Ding, Kuiling Wang, Xingwang
Description	Author Affiliation: Shi L ( State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, PR China.)
Abstract	Well-designed, self-assembled, metal–organic frameworks were constructed by simple mixing of multitopic MonoPhos-based ligands (3; MonoPhos=chiral, monodentate phosphoramidites based on the 1,1′-bi-2-naphthol platform) and $[Rh(cod)_{2}]BF_{4}$ (cod=cycloocta-1,5-diene). This self-supporting strategy allowed for simple and efficient catalyst immobilization without the use of extra added support, giving well-characterized, insoluble (in toluene) polymeric materials (4). The resulting self-supported catalysts (4) showed outstanding catalytic performance for the asymmetric hydrogenation of a number of α-dehydroamino acids (5) and 2-aryl enamides (7) with enantiomeric excess (ee) ranges of 94–98 % and 90–98 %, respectively. The linker moiety in 4 influenced the reactivity significantly, albeit with slight impact on the enantioselectivity. Acquisition of reaction profiles under steady-state conditions showed 4 h and 4 i to have the highest reactivity (turnover frequency (TOF)=95 and $97 h^{−1}$ at 2 atm, respectively), whereas appropriate substrate/catalyst matching was needed for optimum chiral induction. The former was recycled 10 times without loss in ee (95–96 %), although a drop in TOF of approximately 20 % per cycle was observed. The estimation of effective catalytic sites in self-supported catalyst 4 e was also carried out by isolation and hydrogenation of catalyst–substrate complex, showing about 37 % of the $Rh^{I}$ centers in the self-supported catalyst 4 e are accessible to substrate 5 c in the catalysis. A continuous flow reaction system using an activated C/4 h mixture as stationary-phase catalyst for the asymmetric hydrogenation of 5 b was developed and run continuously for a total of 144 h with >99 % conversion and 96–97 % enantioselectivity. The total Rh leaching in the product solution is 1.7 % of that in original catalyst 4 h.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	38
Volume Number	15
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2009-09-28
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Organometallic Compounds Chemistry Organophosphorus Compounds Rhodium Catalysis Hydrogenation Ligands Naphthols Stereoisomerism Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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