Diastereoselective synthesis of (2S)-2-[(R)-1H-indol-3-yl(phenyl)methyl]-2,3-dihydro-1H-inden-1-one

Double asymmetric induction in Michael reactions has been studied. Enantioselective alkylation of a cyclic ketone (1-indanone) with alpha-phenyl-nor-gramine was carried out. The relative configuration of (2S*)-2-[(R*)-1H-indol-3-yl(phenyl)methyl]-2,3-dihydro-1H-inden-1-one was established by X-ray d...

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Published inTetrahedron letters Vol. 47; no. 20; pp. 3479 - 3483
Main Authors Semenov, BB, Novikov, KA, Lysenko, KA, Kachala, VV
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 15.05.2006
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:Double asymmetric induction in Michael reactions has been studied. Enantioselective alkylation of a cyclic ketone (1-indanone) with alpha-phenyl-nor-gramine was carried out. The relative configuration of (2S*)-2-[(R*)-1H-indol-3-yl(phenyl)methyl]-2,3-dihydro-1H-inden-1-one was established by X-ray diffraction. The relative configuration of (R*,R*,S*)- and (S*,R*,S*)-2-1H-indol-3-yl(phenyl)methyl]-2,3-diliydro-1H-inden-1-ols was established by H-1 NMR studies. (c) 2006 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2006.02.158