Bromoallenes as Allyl Dication Equivalents in the Absence of Palladium(0): Synthesis of Bicyclic Sulfamides by Tandem Cyclization of Bromoallenes

Who needs a metal? A highly regioselective synthesis of cyclic sulfamides containing a bicyclo[3.3.0]octane skeleton has been developed (see scheme). The first intramolecular nucleophilic attack of the internal sulfamide nitrogen atom takes place at the central carbon atom of the allenic moiety, and...

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Published inAngewandte Chemie International Edition Vol. 44; no. 10; pp. 1513 - 1517
Main Authors Hamaguchi, Hisao, Kosaka, Shohei, Ohno, Hiroaki, Tanaka, Tetsuaki
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 25.02.2005
WILEY‐VCH Verlag
Wiley
Subjects
allenes
Bromine Compounds - chemistry
Chemistry
Chemistry, Multidisciplinary
Cyclization
halogen compounds
palladium
Palladium - chemistry
Physical Sciences
Science & Technology
Spectrum Analysis - methods
sulfamides
Sulfonamides - chemistry
SERINE PROTEASES
sulfamides
halogen compounds
CYCLIC SULFAMIDE
cyclization
allenes
POTENT
INTRAMOLECULAR AMINATION
palladium
HIV-1 PROTEASE
SELECTIVE SYNTHESIS
STEREOSELECTIVE-SYNTHESIS
INHIBITORS
DERIVATIVES
BINDING
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Summary:Who needs a metal? A highly regioselective synthesis of cyclic sulfamides containing a bicyclo[3.3.0]octane skeleton has been developed (see scheme). The first intramolecular nucleophilic attack of the internal sulfamide nitrogen atom takes place at the central carbon atom of the allenic moiety, and is followed by a second intramolecular nucleophilic addition of the terminal sulfamide nitrogen atom to afford the bicyclic sulfamide.
Bibliography:ark:/67375/WNG-7SRDDFSZ-L
This work was supported by a Grant-in-Aid for Encouragement of Young Scientists from the Ministry of Education, Culture, Sports, Science, and Technology of Japan, and the Mitsubishi Chemical Corporation Fund. H. H. is grateful to Research Fellowships from the Japan Society for the Promotion of Science (JSPS) for Young Scientists.
istex:1A1CDBD1A83403483FC8A2F23A85FE99402E4377
ArticleID:ANIE200462557
This work was supported by a Grant‐in‐Aid for Encouragement of Young Scientists from the Ministry of Education, Culture, Sports, Science, and Technology of Japan, and the Mitsubishi Chemical Corporation Fund. H. H. is grateful to Research Fellowships from the Japan Society for the Promotion of Science (JSPS) for Young Scientists.
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SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200462557