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Asymmetric reduction of aromatic and hetero cyclic ketones by hydrosilylation and hydrogen transfer in the presence of optically active rhodium catalysts

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A study has been made of enantioselective hydrosilylation and reduction, by hydrogen transfer, of prochiral alkyl phenyl ketones or alkyl hetaryl ketones over various optically active catalysts. A total of 14 aromatic and heterocyclic carbinols were synthesized with preparative yields of 54–100%. The most effective catalytic systems were found to be complexes of RhCl3 and [Rh(cod)Cl]2 with the known optical inductor (S,S)-i-Pr-Pybox, with which we have obtained for the first time a series of heterocyclic secondary alcohols with an enantioselectivity of 20–63%.

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Authors
  1. I. Iovel'
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  2. K. Rubina
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  3. Yu. Popelis
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  4. A. Gaukhman
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  5. É. Lukevits
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Additional information

Latvian Institute of Organic Synthesis, Riga, LV-1006. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 342–358, March, 1996. Original article submitted December 11, 1995.

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Iovel', I., Rubina, K., Popelis, Y. et al. Asymmetric reduction of aromatic and hetero cyclic ketones by hydrosilylation and hydrogen transfer in the presence of optically active rhodium catalysts. Chem Heterocycl Compd 32, 294–307 (1996). https://doi.org/10.1007/BF01169246

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