Keteniminium Ion-Initiated Cascade Cationic Polycyclization

A novel and efficient keteniminium-initiated cationic polycyclization is reported. This reaction, which only requires triflic acid or bistriflimide as promoters, affords a straightforward entry to polycyclic nitrogen heterocycles possessing up to three contiguous stereocenters and seven fused cycles...

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Published inJournal of the American Chemical Society Vol. 136; no. 36; pp. 12528 - 12531
Main Authors Theunissen, Cédric, Métayer, Benoît, Henry, Nicolas, Compain, Guillaume, Marrot, Jérome, Martin-Mingot, Agnès, Thibaudeau, Sébastien, Evano, Gwilherm
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 10.09.2014
Amer Chemical Soc
Subjects
Catalysis
Chemical Sciences
Chemistry
Chemistry, Multidisciplinary
Organic chemistry
Other
Physical Sciences
Science & Technology
ELECTROPHILIC REARRANGEMENTS
YNAMIDES
CLAISEN REARRANGEMENTS
ALKYNES
CYCLIZATION
AMIDES
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Summary:A novel and efficient keteniminium-initiated cationic polycyclization is reported. This reaction, which only requires triflic acid or bistriflimide as promoters, affords a straightforward entry to polycyclic nitrogen heterocycles possessing up to three contiguous stereocenters and seven fused cycles. These complex, polycyclic molecules can be obtained in a single operation from readily available ynamides which were shown to be remarkable building blocks for multiple, consecutive cationic transformations.
Bibliography:ObjectType-Article-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja504818p