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(1R,2R)-(−)-2-Dimethylamino-1-(4-nitrophenyl)-1,3- propanediol/l-proline cocatalyzed enantioselective Morita–Baylis–Hillman reaction

Paper ID Volume ID Publish Year Pages File Format Full-Text
52589 46877 2007 4 PDF Available
Title
(1R,2R)-(−)-2-Dimethylamino-1-(4-nitrophenyl)-1,3- propanediol/l-proline cocatalyzed enantioselective Morita–Baylis–Hillman reaction
Abstract

(1R,2R)-(−)-2-Dimethylamino-1-(4-nitrophenyl)-1,3-propanediol (2) was prepared starting from the readily available precursor of antibiotics chloramphenicol. The combination of compound 2 and l-proline have been found to be an efficient cocatalyst for the asymmetric Morita–Baylis–Hillman (MBH) reaction between methyl vinyl ketone (MVK) and aromatic aldehydes. The corresponding adducts were formed in reasonable chemical yields with good enantioselectivities (up to 82% ee). Performance of parallel cocatalytic reactions with chiral amine 2 and the two enantiomers of proline revealed that it is the proline stereochemistry that determines the configuration of the newly formed chiral center.

Keywords
(1R,2R)-(−)-2-Dimethylamino-1-(4-nitrophenyl)-1,3-propanediol; Cocatalyst; Asymmetric Morita–Baylis–Hillman reaction; Enantioselectivity
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(1R,2R)-(−)-2-Dimethylamino-1-(4-nitrophenyl)-1,3- propanediol/l-proline cocatalyzed enantioselective Morita–Baylis–Hillman reaction
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 8, Issue 11, November 2007, Pages 1811–1814
Authors
, , , , , ,
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
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us