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

Authors

  • И. Иовель Latvian Institute of Organic Synthesis, Riga LV-1006
  • K. Рубина Latvian Institute of Organic Synthesis, Riga LV-1006
  • Ю. Попелис Latvian Institute of Organic Synthesis, Riga LV-1006
  • А. Гаухман Latvian Institute of Organic Synthesis, Riga LV-1006
  • Э. Лукевиц Latvian Institute of Organic Synthesis, Riga LV-1006

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%.

How to Cite
Iovel', I.; Rubina, K.; Popelis, Yu.; Gaukhman, A.; Lukevits, E. Chem. Heterocycl. Compd. 1996, 32, 294. [Khim. Geterotsikl. Soedin. 1996, 342.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01169246

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Published

1996-03-25

Issue

No. 3 (1996)

Section

Original Papers