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Synlett 2011(4): 485-488  
DOI: 10.1055/s-0030-1259543
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© Georg Thieme Verlag Stuttgart ˙ New York

Diarylprolinol in the Direct Asymmetric Aldol Reaction of Trifluoromethylacetaldehyde Ethyl Hemiacetal with Aldehyde

Yujiro Hayashi*, Yusuke Yasui, Tsuyoshi Kawamura, Masahiro Kojima, Hayato Ishikawa
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku,Tokyo 162-8601, Japan
Fax: +81(3)52614631; e-Mail: hayashi@ci.kagu.tus.ac.jp;
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Received 12 December 2010
Publikationsdatum:
08. Februar 2011 (online)

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Erratum zu diesem Artikel:

Diarylprolinol in the Direct Asymmetric Aldol Reaction of Trifluoromethylacetaldehyde Ethyl Hemiacetal with AldehydeSynlett 2011; 2011(12): 1788-1788
DOI: 10.1055/s-0029-1260945

Abstract

Asymmetric direct aldol reaction of trifluoromethylacet­aldehyde with aldehyde using diarylprolinol as a catalyst, to afford a synthetically useful β-trifluoromethyl-β-hydroxy aldehyde with excellent enantioselectivity, was developed. Commercially available trifluoromethylacetaldehyde ethyl hemiacetal was used directly as a precursor of trifluoromethylacetaldehyde without acid pyrolysis or distillation prior to use.

Key words

asymmetric synthesis - aldol reactions - organocatalyst - diarylprolinol - trifluoromethylacetaldehyde

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12

TCI, catalog number T0791.

13

When the reaction was performed in 72 h, the yield increased to 49% but the anti/syn ratio decreased to 3.5:1, which indicates that the partial isomerization occurred during the reaction.