Transfer of Chirality in the Rhodium-Catalyzed Intramolecular Formal Hetero-[5 + 2] Cycloaddition of Vinyl Aziridines and Alkynes: Stereoselective Synthesis of Fused Azepine Derivatives

By taking advantage of vinyl aziridines as a heteroatom-containing five-atom component in rhodium-catalyzed intramolecular formal hetero-[5 + 2] cycloaddition reactions with alkynes, a highly efficient method for the synthesis of fused azepine derivatives at 30 °C was developed. The reaction has bro...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 137; no. 11; pp. 3787 - 3790
Main Authors Feng, Jian-Jun, Lin, Tao-Yan, Wu, Hai-Hong, Zhang, Junliang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.03.2015
Amer Chemical Soc
Subjects
alkynes
Chemistry
Chemistry, Multidisciplinary
cycloaddition reactions
Physical Sciences
Science & Technology
standard operating procedures
stereochemistry
stereoisomerism
REARRANGEMENT
INTERMOLECULAR 5+2 CYCLOADDITION
HETEROCYCLES
7-MEMBERED RINGS
ISOMERIZATION
REACTIVITY
3-ACYLOXY-1,4-ENYNES
VINYLCYCLOPROPANES
SELECTIVITY
CYCLIZATION
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Summary:By taking advantage of vinyl aziridines as a heteroatom-containing five-atom component in rhodium-catalyzed intramolecular formal hetero-[5 + 2] cycloaddition reactions with alkynes, a highly efficient method for the synthesis of fused azepine derivatives at 30 °C was developed. The reaction has broad substrate scope and tolerates a wide range of functional groups. The chirality of vinyl aziridine-alkyne substrates can be completely transferred to the cycloadducts, representing an atom-economic and enantiospecific protocol for the construction of fused 2,5-dihydroazepines for the first time.
Bibliography:ObjectType-Article-1
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.5b01305