Document Detail


Asymmetric Trisubstituted Aziridination of Aldimines and Ketimines using N-α-Diazoacyl Camphorsultams.
MedLine Citation:
PMID:  21069659     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
The acid-catalyzed reaction of diazoacetates and aldimines (Brookhart-Templeton aziridination) is now recognized as a reliable method to provide enantiomerically enriched disubstituted aziridines, thus owing to the development of asymmetric catalysis. However, the extension of this method to prepare trisubstituted aziridines has not been explored to date, even for racemic products. In this context, and considering their synthetic importance and lack of alternative direct synthetic methods, we recently launched a program to realize this unmet challenge. Herein, we report a detailed study, which led to the establishment of a highly stereoselective synthesis for various trisubstituted aziridines, building on the use of N-α-diazoacyl camphorsultams as a key component.
Authors:
Takuya Hashimoto; Hiroki Nakatsu; Kumiko Yamamoto; Shogo Watanabe; Keiji Maruoka
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2010-11-10
Journal Detail:
Title:  Chemistry, an Asian journal     Volume:  -     ISSN:  1861-471X     ISO Abbreviation:  -     Publication Date:  2010 Nov 
Date Detail:
Created Date:  2010-11-11     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101294643     Medline TA:  Chem Asian J     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502 (Japan), Fax: (+81) 75-753-4041.
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