A mild and efficient synthesis of 2,5-disubstituted 2,3-dihydro-4-pyridones catalyzed by Yb(OTf)(3)

A highly efficient aza-Diels-Alder reaction of trans-1-methoxy-2-methyl-3-trimethylsiloxybuta-1,3-diene with N-benz-hydryl imines was catalyzed by Yb(OTf)(3) in toluene at room temperature to give corresponding 2,5-disubstituted 2,3-dihydro-4pyridones in high yields. Three-component reactions of die...

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Bibliographic Details
Published inSynlett no. 6; pp. 1018 - 1020
Main Authors Cheng, K, Zeng, BQ, Yu, ZP, Gao, B, Feng, XM
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 06.04.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Lewis acid
BORON REAGENT
DANISHEFSKYS DIENE
N-benzhydryl imines
ENANTIOSELECTIVE SYNTHESIS
SOLID-PHASE
ALPHA-AMINO-ACIDS
solvent-free
AZA-DIELS-ALDER
three-component reaction
TRIFLATE
LEWIS-ACID CATALYSTS
QUINOLINE DERIVATIVES
Diels-Alder reaction
N-SULFONYL IMINES
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Summary:A highly efficient aza-Diels-Alder reaction of trans-1-methoxy-2-methyl-3-trimethylsiloxybuta-1,3-diene with N-benz-hydryl imines was catalyzed by Yb(OTf)(3) in toluene at room temperature to give corresponding 2,5-disubstituted 2,3-dihydro-4pyridones in high yields. Three-component reactions of diene with aldehydes and amines were also performed smoothly to afford the desired cycloadducts under solvent-free condition in 51-86% yields.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2005-864810