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Issue 21, 2011
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Synthesis of 2,3,5,6-tetrahydro-1-alkyl/aryl-1H-benzo[f]chromen-3-ol derivatives from β-tetralones and α,β-unsaturated aldehydes

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Abstract

Organocatalytic domino Michael–hemiacetalization of β-tetralones with α,β-unsaturated aldehydes is presented. Treatment of β-tetralones with α,β-unsaturated aldehydes in the presence of diphenylprolinol silyl ether gave 2,3,5,6-tetrahydro-1-alkyl/aryl-1H-benzo[f]chromen-3-ol derivatives with high to excellent chemical yields (50–99%) and high levels of enantioselectivities (up to 96% ee).

Graphical abstract: Synthesis of 2,3,5,6-tetrahydro-1-alkyl/aryl-1H-benzo[f]chromen-3-ol derivatives from β-tetralones and α,β-unsaturated aldehydes

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Publication details

The article was received on 15 Jun 2011, accepted on 05 Aug 2011 and first published on 08 Aug 2011


Article type: Paper
DOI: 10.1039/C1OB05966A
Citation: Org. Biomol. Chem., 2011,9, 7510-7516
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    Synthesis of 2,3,5,6-tetrahydro-1-alkyl/aryl-1H-benzo[f]chromen-3-ol derivatives from β-tetralones and α,β-unsaturated aldehydes

    J. Chen, C. Chang, H. Chang and K. Chen, Org. Biomol. Chem., 2011, 9, 7510
    DOI: 10.1039/C1OB05966A

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