One-Pot Highly Diastereoselective Synthesis of cis-Vinylaziridines via the Sulfur Ylide-Mediated Aziridination and Palladium(0)-Catalyzed Isomerization

Highly diastereoselective synthesis of cis-trisubstituted vinylaziridines containing a quaternary carbon center is realized by a one-pot protocol in which the combination of sulfur ylide-mediated aziridination of cyclic ketimines and Pd(0)-catalyzed isomerization is employed successfully.

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Bibliographic Details
Published inOrganic letters Vol. 12; no. 3; pp. 504 - 507
Main Authors Zhu, Ben-Hu, Zheng, Jun-Cheng, Yu, Chang-Bin, Sun, Xiu-Li, Zhou, Yong-Gui, Shen, Qi, Tang, Yong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.02.2010
Amer Chemical Soc
Subjects
Aziridines - chemical synthesis
Aziridines - chemistry
Catalysis
Chemistry
Chemistry, Organic
Molecular Structure
Palladium - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Sulfur Compounds - chemistry
Vinyl Compounds - chemical synthesis
Vinyl Compounds - chemistry
VINYL
OLEFINATION
ENANTIOSELECTIVE SYNTHESIS
IMINE AZIRIDINATION
ASYMMETRIC AZIRIDINATION
THERMODYNAMIC PREFERENCE
STEREOSELECTIVE-SYNTHESIS
CHIRAL AZIRIDINES
N-SULFONYLIMINES
NITRENE
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Summary:Highly diastereoselective synthesis of cis-trisubstituted vinylaziridines containing a quaternary carbon center is realized by a one-pot protocol in which the combination of sulfur ylide-mediated aziridination of cyclic ketimines and Pd(0)-catalyzed isomerization is employed successfully.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol9027072