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Acta Chimica Sinica >

2014 , Vol. 72 >Issue 7: 820 - 824

DOI: https://doi.org/10.6023/A14050391

Communication

Application of Chiral Anion Metathesis Strategy in Asymmetric Transfer Hydrogenation of Isoquinolines

  • Shi LeiJi ,
  • Yue Huang ,
  • Wen xue ,
  • Zhou Yonggui
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  • a Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China;
    b State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China

Received date: 2014-05-19

  Online published: 2014-06-17

Supported by

Project supported by the National Natural Science Foundation of China (No. 21202162) and the State Key Laboratory of Fine Chemicals (No. KF1110).

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Abstract

Asymmetric hydrogenation of N-hetero aromatics offers a very straightforward and efficient method to obtain the corresponding chiral N-hetero cyclic saturated or partially saturated compounds. As one of the most challenging substrates, asymmetric hydrogenation of isoquinolines has met with limited success probably because of lower reactivity and the catalyst deactivation resulted from strong coordination. Considering the prevalence of the chiral 1,2,3,4-tetrahydroisoquinoline motif in natural alkaloids and drug molecules, the development of new catalyst system for asymmetric hydrogenation of isoquinolines is highly desirable and significant. Herein, a novel chiral anion metathesis strategy successfully applied for asymmetric transfer hydrogenation of isoquinolines is reported. N-Protected 1-substituted 1,2-dihydroisoquinolines were obtained with high yield and up to 79% ee in the presence of Hantzsch ester and chloroformate using chiral phosphoric acid as catalyst. The phosphate salt and the activated N-acyl isoquinolinium chloride undergo anion metathesis to form chiral contact ion pair, which leads to a highly enantioselective transfer hydrogenation of isoquinolines. After systematically investigating the effects of activating reagent, solvent, base, hydride donor and catalyst on this transfer hydrogenation reaction, the best result was achieved under the optimized condition as follows: 5 mol% H8-BINOL-derived chiral phosphoric acid as catalyst, 1.2 equivalent 2,2,2-trichloroethyl chloroformate as activator, 1.5 equivalent dimethyl 2,6-diethyl-1,4-dihydropyridine-3,5- dicarboxylate as hydride donor, 1.5 equivalent sodium carbonate as base and cyclohexane as solvent. The reaction is tolerant toward a broad range of aryl or alkyl 1-substituted isoquinoline substrates. This methodology represents one of the rare examples of asymmetric hydrogenation of this challenging substrate. The utilizing of chiral anion metathesis strategy could enable chiral phosphoric acid to catalyze more asymmetric transformation process and further researching is ongoing in our laboratory.

Key words： chiral phosphoric acid; chiral anion metathesis; transfer hydrogenation; isoquinolines

Cite this article

Shi LeiJi , Yue Huang , Wen xue , Zhou Yonggui . Application of Chiral Anion Metathesis Strategy in Asymmetric Transfer Hydrogenation of Isoquinolines[J]. Acta Chimica Sinica, 2014 , 72(7) : 820 -824 . DOI: 10.6023/A14050391

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