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The state of art in the practical heterogeneous catalytic synthesis of chiral compounds is reviewed in the light of the fundamental features of chiral surfaces

Asymmetric catalysis at chiral metal surfaces.

CHEMICAL REVIEWS, no. 11.0 (2007): 4863-4890

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摘要

Tamas Mallat received an M.S. degree in 1972 in Chemical Engineering and a Ph.D. in 1976 in Technical Chemistry, both from the Technical University of Budapest, Hungary. He was a postdoctoral associate at Brunel University, London, from 1978 to 1979. He continued his academic carrier at the Organic Chemical Technology Research Group of th...更多

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简介
  • Tamas Mallat received an M.S. degree in 1972 in Chemical Engineering and a Ph.D. in 1976 in Technical Chemistry, both from the Technical University of Budapest, Hungary.
  • Adsorption and catalysis.[14,15,16,17,18,19,20,21] From a practical catalysis point of view, the most promising solid enantioselective catalysts are metals modified by the addition of a soluble chiral compound
  • This approach, which is the main topic of the present review, will be considered in sections 3-5.
  • The disappointing results are understandable when considering that only a fraction of the total surface metal atoms, those at the metal/support interface, are in direct contact with the chiral support, whereas on the rest of the
重点内容
  • Tamas Mallat received an M.S. degree in 1972 in Chemical Engineering and a Ph.D. in 1976 in Technical Chemistry, both from the Technical University of Budapest, Hungary
  • From a practical catalysis point of view, the most promising solid enantioselective catalysts are metals modified by the addition of a soluble chiral compound
  • Other chiral solids that are less attractive for asymmetric synthesis are shortly reviewed here
  • In the complex reaction route (Scheme 4), the medium ee in the first step is increased up to 90% via further transformation of the hydroxy-ketone intermediate to the 1,2diol
  • The state of art in the practical heterogeneous catalytic synthesis of chiral compounds is reviewed in the light of the fundamental features of chiral surfaces
结果
  • The only synthetic modifier that offers better than 90% ee is pantoylnaphthylethylamine (PNEA) (Figure 3).[56].
  • Better than 90% ee has been reported for R-ketoesters,[60,61] ketopantolactone,[62] pyrrolidine-triones,[63] R-ketoacetals,[64,65] R-ketoethers,[66] R-diketones,[67] and R,R,Rtrifluoromethyl ketones[56,68] (Figure 5).
  • Hydrogenation of R-ketoamides on CDmodified Pt/Al2O3 is not an attractive route to the corresponding chiral alcohols (34-60% ee),[278,279,280] but reduction of cyclic imidoketones, such as pyrrolidine-2,3,5-triones, affords up to 91% ee (Figure 5).[63,281].
  • CN-modified Pd/BaSO4 in the presence of NBu3 as a HCl acceptor afforded the monochloride with high chemoselectivity and up to 50% ee
结论
  • The state of art in the practical heterogeneous catalytic synthesis of chiral compounds is reviewed in the light of the fundamental features of chiral surfaces.
  • Despite the remarkable development in the past years, many details of the interaction of substrate and chiral modifier at the metal surface remain to be worked out.
  • The authors hope that this critical review aids in improving the understanding of enantioselection at the molecular level and provokes further research in this fascinating area of heterogeneous catalysis.
  • From a synthetic point of view, the simple approach of chiral modification of metals provides easy-to-handle catalysts that in some reactions are highly efficient and represent a technically attractive and cheap alternative to soluble transition metal complex catalysts
表格
  • Table1: Steric and Electronic Effects in the Hydrogenation of r-Ketoesters on 5 wt % Pt/Al2O3 Modified by CD, QN, and O-Phenyl-cinchonidine (PhOCD) (Toluene, 10 bar, r.t.)[<a class="ref-link" id="c217" href="#r217">217</a>] tioselection. This conclusion is supported by the observation that hydrogenation of the deactivated ketone acetophenone on the Pt-CD system is poorly selective, but introduction of electron-withdrawing CF3 groups in the phenyl ring [in 3,5-bis-(trifluoromethyl)acetophenone] enhanced the ee up to 60%.220
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基金
  • Financial support from the Swiss National Science Foundation and the Foundation Claude and Giuliana is gratefully acknowledged
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