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Abstract
A new type of NADH model compound has been synthesized by an efficient and convenient method. This model compound exhibits high reactivity and enantioselectivity in asymmetric reduction reactions. The results show that chiral NADH model S could be effectively combined with Mg2+ to form ternary complexes. This novel C3 symmetrical NADH model is capable of fluorescence emission at 460 nm when excited at 377 nm.
Highlights
The study of Nicotinamide adenine dinucleotide (NADH) and its phosphate derivative (NADPH) is an active research field in organic chemistry and biochemistry[1,2]
Compared to the various examples of catalytic asymmetric transfer hydrogenation reactions of C= C and C= N double bonds mediated by Hantzsch esters, fairly limited work has been reported on asymmetric hydrogenation reactions of C= O double bonds by chiral NADH models[13]
Inspired by Ohno’s introduction of (R)-α -methylbenzylamine into the NADH model 1 and the first C3 symmetrical NADH model 4 which are shown in Fig. 1, a new C3-symmetric chiral NADH model S bearing dihydropyridine amido group was synthesized. (R)-α -methylbenzylamine is introduced as the chiral source to connect three identical pyridine-3,5-dicarbonyl groups into three “petal”
Summary
The study of Nicotinamide adenine dinucleotide (NADH) and its phosphate derivative (NADPH) is an active research field in organic chemistry and biochemistry[1,2]. Design and synthesis of novel and efficient chiral NADH models for asymmetric reduction of C= O double bond with high enantioselectivity remain an urgent and challenging research topic. In the past few decades, many chiral NADH models with C1 and C2-symmetry have been designed and synthesized respectively[19,20,21,22,23]. These models contain one or two dihydropyridine amido groups, which could not take full advantage of the dihydropyridine amido groups as chiral hydrogen sources. Which could encase and fix certain substrates to accomplish the biomimetic reduction with high yields and enantioselectivity[18]
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