Enantioselective Friedel−Crafts Alkylations with Benzoylhydrazones Promoted by a Simple Strained Silacycle Reagent

The enantioselective Friedel−Crafts reaction of electron-rich arenes and heteroarenes with the benzoylhydrazone of isopropyl glyoxylate mediated by a simple chiral silane Lewis acid is described. The reactions are highly practical, as demonstrated by a larger scale (5 g of the hydrazone) reaction in...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 127; no. 9; pp. 2858 - 2859
Main Authors Shirakawa, Seiji, Berger, Richard, Leighton, James L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 09.03.2005
Amer Chemical Soc
Subjects
Chemical reactivity
Chemistry
Chemistry, Multidisciplinary
Exact sciences and technology
Organic chemistry
Physical Sciences
Reactivity and mechanisms
Science & Technology
CATALYSIS
IMINES
ALLYLATION
ESTERS
LEWIS-BASE ACTIVATION
ALPHA-AMINO-ACIDS
ALDEHYDES
ADDITIONS
BOND
Five membered ring
Catalytic reaction
Friedel Crafts reaction
Enantioselectivity
Catalyst selectivity
Homogeneous catalysis
Oxygen nitrogen silicon heterocycle
Hydrazone
Experimental study
Catalyst activity
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Summary:The enantioselective Friedel−Crafts reaction of electron-rich arenes and heteroarenes with the benzoylhydrazone of isopropyl glyoxylate mediated by a simple chiral silane Lewis acid is described. The reactions are highly practical, as demonstrated by a larger scale (5 g of the hydrazone) reaction in which the recovery of the pseudoephedrine in 99% yield was achieved. A simple model is advanced to explain the observed enantioselectivity.
Bibliography:istex:504CB7CC1FB820ACE05B731D3D402A1B4A1BB81D
ark:/67375/TPS-F6G08MDC-8
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja042522a