An Isothiourea-Catalyzed Asymmetric [2,3]-Rearrangement of Allylic Ammonium Ylides

Benzotetramisole promotes the catalytic asymmetric [2,3]-rearrangement of allylic quaternary ammonium salts (either isolated or prepared in situ from p-nitrophenyl bromoacetate and the corresponding allylic amine), generating syn-α-amino acid derivatives with excellent diastereo- and enantioselectiv...

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Published inJournal of the American Chemical Society Vol. 136; no. 12; pp. 4476 - 4479
Main Authors West, Thomas H, Daniels, David S. B, Slawin, Alexandra M. Z, Smith, Andrew D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 26.03.2014
Amer Chemical Soc
Subjects
Alkenes - chemistry
Ammonium Compounds - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Stereoisomerism
Substrate Specificity
Thiourea - chemistry
REARRANGEMENT
ARYL PHENYLACETATES
CARBENE
ONE-POT SYNTHESIS
KINETIC RESOLUTION
BENZOTETRAMISOLE
AMINO-ACID DERIVATIVES
REACTIVITY
KETENE-FORMING ELIMINATIONS
ORGANOCATALYTIC ACTIVATION
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Summary:Benzotetramisole promotes the catalytic asymmetric [2,3]-rearrangement of allylic quaternary ammonium salts (either isolated or prepared in situ from p-nitrophenyl bromoacetate and the corresponding allylic amine), generating syn-α-amino acid derivatives with excellent diastereo- and enantioselectivity (up to >95:5 dr; up to >99% ee).
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ObjectType-Article-1
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content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja500758n