Search for Dipolarophile Structure Influence upon
Stereochemistry of Cycloadducts in 1,3-Dipolar Cycloaddition of
Azomethine Ylides Generated from N-(-)-Menthyloxycarbonylmethyl
phenanthridinium

D 2001

Search for Dipolarophile Structure Influence upon Stereochemistry of Cycloadducts in 1,3-Dipolar Cycloaddition of Azomethine Ylides Generated from N-(-)-Menthyloxycarbonylmethyl phenanthridinium

TRÁVNÍČEK, Martin and Milan POTÁČEK

Basic information

Original name

Search for Dipolarophile Structure Influence upon Stereochemistry of Cycloadducts in 1,3-Dipolar Cycloaddition of Azomethine Ylides Generated from N-(-)-Menthyloxycarbonylmethyl phenanthridinium

Authors

TRÁVNÍČEK, Martin and Milan POTÁČEK

Edition

1. vyd. Prague, Czech Republic, Book of Abstracts - 9th Meeting on Stereochemistry, p. 177-178, 2001

Publisher

Instituteof Chemical Technology, Prague

Other information

Language

English

Type of outcome

Stať ve sborníku

Field of Study

10401 Organic chemistry

Country of publisher

Czech Republic

Confidentiality degree

není předmětem státního či obchodního tajemství

Organization unit

Faculty of Science

ISBN

80-7080-427-0

Keywords in English

1;3-dipolar cycloaddition; chiral auxiliary; azomethine ylides; stereochemistry; structure

Abstract

V originále

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.

Links

MSM 143100011, plan (intention)

Name: Struktura a vazebné poměry, vlastnosti a analýza syntetických a přírodních molekulových ansamblů

Investor: Ministry of Education, Youth and Sports of the CR, Structure and character of bonding, properties and analysis of synthetic and natural molecular ensembles

Citovat

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 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.

@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.

Detailed Information on Publication Record