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@inproceedings{374973,
author = {Trávníček, Martin and Potáček, Milan},
address = {Prague, Czech Republic},
booktitle = {Book of Abstracts - 9th Meeting on Stereochemistry},
edition = {1.},
keywords = {1;3-dipolar cycloaddition; chiral auxiliary; azomethine ylides; stereochemistry; structure},
language = {eng},
location = {Prague, Czech Republic},
isbn = {80-7080-427-0},
pages = {177-178},
publisher = {Instituteof Chemical Technology, Prague},
title = {Search for Dipolarophile Structure Influence upon Stereochemistry of Cycloadducts in 1,3-Dipolar Cycloaddition of Azomethine Ylides Generated from N-(-)-Menthyloxycarbonylmethyl phenanthridinium},
year = {2001}
}
TY - JOUR
ID - 374973
AU - Trávníček, Martin - Potáček, Milan
PY - 2001
TI - Search for Dipolarophile Structure Influence upon Stereochemistry of Cycloadducts in 1,3-Dipolar Cycloaddition of Azomethine Ylides Generated from N-(-)-Menthyloxycarbonylmethyl phenanthridinium
PB - Instituteof Chemical Technology, Prague
CY - Prague, Czech Republic
SN - 8070804270
KW - 1;3-dipolar cycloaddition
KW - chiral auxiliary
KW - azomethine ylides
KW - stereochemistry
KW - structure
N2 - Prepared (-)-menthyl - bromoacetate underwent a nucleophilic substitution reaction with the phenanthridine nitrogen atom under formation of N-(-)-menthyloxy-carbonylmethyl phenanthridinium.Generated azomethine ylides were searched in reactions with various olefines.Determination of relative configuration on atoms has been based on NMR measurements of interaction constants values. Non-symmetrical dipolarophiles are expected to form two regioisomers. Their formation has been determined by COSY and HMBC experiments based on H atoms interactions with carbonyl and nitrile carbon atom bound at C1 and C2 atoms, respectively. In all the cases only one regioisomer has been found. Chromatographically purified compounds were separated by HPLC on nonracemic sorbent based on cellulose. A detector UV (260 nm) and JASCO CD 995 (260 nm) for identification of enantiomers were used.
ER -
TRÁVNÍČEK, Martin and Milan POTÁČEK. Search for Dipolarophile Structure Influence upon Stereochemistry of Cycloadducts in 1,3-Dipolar Cycloaddition of Azomethine Ylides Generated from N-(-)-Menthyloxycarbonylmethyl phenanthridinium. In \textit{Book of Abstracts - 9th Meeting on Stereochemistry}. 1st ed. Prague, Czech Republic: Instituteof Chemical Technology, Prague, 2001, p.~177-178. ISBN~80-7080-427-0.
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