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

Jung Hsuan Chen; Chihliang Chang; Hui Ju Chang; Kwunmin Chen

doi:10.1039/c1ob05966a

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

Jung Hsuan Chen, Chihliang Chang, Hui Ju Chang, Kwunmin Chen

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

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).

Original language	English
Pages (from-to)	7510-7516
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	9
Issue number	21
DOIs	https://doi.org/10.1039/c1ob05966a
Publication status	Published - 2011 Nov 7

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "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",

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).",

author = "Chen, {Jung Hsuan} and Chihliang Chang and Chang, {Hui Ju} and Kwunmin Chen",

year = "2011",

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doi = "10.1039/c1ob05966a",

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volume = "9",

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journal = "Organic and Biomolecular Chemistry",

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publisher = "Royal Society of Chemistry",

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T1 - 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

AU - Chen, Jung Hsuan

AU - Chang, Chihliang

AU - Chang, Hui Ju

AU - Chen, Kwunmin

PY - 2011/11/7

Y1 - 2011/11/7

N2 - 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).

AB - 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).

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