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Enantioselective addition of diethylzinc to aldehydes catalyzed by d-glucosamine derivatives: Highly pronounced effect of trifluoromethylsulfonamide

Paper ID Volume ID Publish Year Pages File Format Full-Text
42478 45927 2010 5 PDF Available
Title
Enantioselective addition of diethylzinc to aldehydes catalyzed by d-glucosamine derivatives: Highly pronounced effect of trifluoromethylsulfonamide
Abstract

We present the synthesis of β-hydroxy sulfonamides derived from d-glucosamine and their application as ligands in titanium tetraisopropoxide promoted enantioselective addition of diethylzinc to benzaldehyde and selected aromatic and aliphatic aldehydes. The N-trifluoromethylosulfonamido-d-glucosamine derivative is one of the most active ligands known and only 1 mol% of the ligand is sufficient for efficient catalysis of diethylzinc addition. The reaction is highly enantioselective for some aromatic aldehydes and enantiomeric excess up to 99% was obtained.

Graphical abstractWe present the synthesis of β-hydroxy sulfonamides derived from d-glucosamine and their application as ligands in titanium tetraisopropoxide promoted enantioselective addition of diethylzinc to benzaldehyde and selected aromatic and aliphatic aldehydes. The reaction is highly enantioselective for some aromatic aldehydes and enantiomeric excess up to 99% was obtained.Figure optionsDownload full-size imageDownload high-quality image (37 K)Download as PowerPoint slide

Keywords
d-Glucosamine; Diethylzinc; Titanium tetraisopropoxide; Enantioselective; Trifluoromethylsulfonamide
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Enantioselective addition of diethylzinc to aldehydes catalyzed by d-glucosamine derivatives: Highly pronounced effect of trifluoromethylsulfonamide
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 375, Issue 2, 1 March 2010, Pages 247–251
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
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Full-text PDF Download
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Any Questions? feel free to contact us