Torquoselective Ring Closures of Chiral Amido Trienes Derived from Allenamides. A Tandem Allene Isomerization−Pericyclic Ring-Closure−Intramolecular Diels−Alder Cycloaddition

A new torquoselective ring-closure of chiral amide-substituted 1,3,5-hexatrienes and its application in tandem with [4 + 2] cycloaddition are described. The trienes were derived via either a 1,3-H or 1,3-H−1,7-H shift of α-substituted allenamides, and the entire sequence through the [4 + 2] cycloadd...

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Bibliographic Details
Published inOrganic letters Vol. 12; no. 6; pp. 1152 - 1155
Main Authors Hayashi, Ryuji, Feltenberger, John B, Hsung, Richard P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.03.2010
Amer Chemical Soc
Subjects
Amides - chemistry
Chemistry
Chemistry, Organic
Crystallography, X-Ray
Cyclization
Models, Molecular
Molecular Conformation
Physical Sciences
Polyenes - chemical synthesis
Polyenes - chemistry
Science & Technology
Stereoisomerism
DIENES
1,3,5-HEXATRIENES
HYDROGEN SHIFT
2-AMINO-1,3-BUTADIENES
ELECTROCYCLIZATIONS
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Summary:A new torquoselective ring-closure of chiral amide-substituted 1,3,5-hexatrienes and its application in tandem with [4 + 2] cycloaddition are described. The trienes were derived via either a 1,3-H or 1,3-H−1,7-H shift of α-substituted allenamides, and the entire sequence through the [4 + 2] cycloaddition could be in tandem from allenamides.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol902821w