Jump to main content
Jump to site search

Issue 17, 2015
Previous Article Next Article

Application of chiral ligands: carbohydrates, nucleoside-lanthanides and other Lewis acid complexes to control regio- and stereoselectivity of the dipolar cycloaddition reactions of nitrile oxides and esters

Author affiliations

Abstract

Chiral Lewis acid mediated 1,3-dipolar cycloaddition reactions of 4-trifluoromethylbenzonitrile oxide to methyl crotonate as well to β-substituted acrylates and (Z)-pent-2-en-1-yl esters were examined. Excellent enantioselectivities with moderate to good regioselectivities were achieved for crotonates with complexes of BiBr3 with (+)-(4,6-benzylidene)methyl-α-D-glucopyranoside C, with the L-ascorbic acid I–FeCl3 system, and with lipase Candida antarctica. High enantiomeric excess was observed for isopropyl ester and benzyl ester. The outstanding ee values were achieved for acrylates with β-t-butyl, cyclohexyl, and 1,3-benzodioxol-5-yl groups in cycloadditions catalyzed by C–Yb(OTf)3 and the (+)-2-hydroxy-3-pinanone N–TiCl4 system. High enantioselectivities were found in reactions of (Z)-pent-2-en-1-yl esters mediated by complexes N–Mg(OTf)2 and N–TiCl4.

Graphical abstract: Application of chiral ligands: carbohydrates, nucleoside-lanthanides and other Lewis acid complexes to control regio- and stereoselectivity of the dipolar cycloaddition reactions of nitrile oxides and esters

Back to tab navigation

Supplementary files

Publication details

The article was received on 08 Dec 2014, accepted on 16 Jan 2015 and first published on 26 Jan 2015


Article type: Paper
DOI: 10.1039/C4RA15975F
RSC Adv., 2015,5, 13112-13124

  •   Request permissions

    Application of chiral ligands: carbohydrates, nucleoside-lanthanides and other Lewis acid complexes to control regio- and stereoselectivity of the dipolar cycloaddition reactions of nitrile oxides and esters

    M. Gucma, W. M. Gołębiewski and M. Krawczyk, RSC Adv., 2015, 5, 13112
    DOI: 10.1039/C4RA15975F

Search articles by author

Spotlight

Advertisements