Formal [3+2] Cycloaddition of Ketenes and Oxaziridines Catalyzed by Chiral Lewis Bases: Enantioselective Synthesis of Oxazolin‐4‐ones

Choose the right cat.: A highly enantioselective synthesis of oxazolin‐4‐ones by the formal [3+2] cycloaddition of ketenes and a racemic oxaziridines has been developed (see scheme; cat.=N‐heterocyclic carbenes for disubstituted ketenes or cinchona alkaloids for monosubstituted ketenes, Ts=4‐toluene...

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Published inAngewandte Chemie (International ed.) Vol. 49; no. 45; pp. 8412 - 8416
Main Authors Shao, Pan‐Lin, Chen, Xiang‐Yu, Ye, Song
Format Journal Article
LanguageEnglish
Published Weinheim Wiley‐VCH Verlag 02.11.2010
WILEY-VCH Verlag
WILEY‐VCH Verlag
Wiley
Subjects
asymmetric catalysis
Chemistry
Chemistry, Multidisciplinary
cycloaddition
ketenes
oxaziridines
oxazolidin-4-ones
Physical Sciences
Science & Technology
OXIDATION
INTERMOLECULAR STETTER REACTIONS
ASYMMETRIC-SYNTHESIS
ACID
oxazolidin-4-ones
HYDROXYLATION
ALDEHYDES
asymmetric catalysis
EPOXIDATION
cycloaddition
oxaziridines
ketenes
BETA-LACTONES
CHEMISTRY
DERIVATIVES
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Summary:Choose the right cat.: A highly enantioselective synthesis of oxazolin‐4‐ones by the formal [3+2] cycloaddition of ketenes and a racemic oxaziridines has been developed (see scheme; cat.=N‐heterocyclic carbenes for disubstituted ketenes or cinchona alkaloids for monosubstituted ketenes, Ts=4‐toluenesulfonyl).
Bibliography:http://dx.doi.org/10.1002/anie.201003532
Chinese Academy of Sciences
istex:22A966F29CCCC6F69D198D0BD38D25594373FA84
ark:/67375/WNG-H2DP6C42-9
Financial support from the National Natural Science Foundation of China (nos. 20872143, 20932008), the Ministry of Science and Technology of China (no. 2009ZX-5909501-018), and the Chinese Academy of Sciences is gratefully acknowledged.
National Natural Science Foundation of China - No. 20872143; No. 20932008
Ministry of Science and Technology of China - No. 2009ZX-5909501-018
ArticleID:ANIE201003532
Financial support from the National Natural Science Foundation of China (nos. 20872143, 20932008), the Ministry of Science and Technology of China (no. 2009ZX‐5909501‐018), and the Chinese Academy of Sciences is gratefully acknowledged.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201003532