Electrophile-and Lewis acid-induced nitrone formation and 1,3- dipolar cycloaddition reactions in the 13α- and 13β-estrone series

E. Mernyák, Judit Huber, Gabriella Benedek, Roland Pfoh, Stephan Rühl, G. Schneider, János Wölflinga

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

δ-Alkenyl oximes of 13a-estrone 3-methyl ether undergo intramolecular 1,3-dipolar cycloaddition reactions with BF3-OEt2 as catalyst, furnishing isoxazolidines. The reactions of the 13a- and 13β-estrone oximes with electrophiles lead to cyclic nitrones in high yields via attack of the oxime nitrogen on the intermediate halonium ions. In the intermolecular cycloadditions of 16-halomethyl nitrones to N-phenylmaleimide, single condensed aza-D-homo isoxazolidines are formed with high chemo- and stereoselectivity.

Original languageEnglish
Pages (from-to)101-113
Number of pages13
JournalArkivoc
Volume2010
Issue number11
Publication statusPublished - Sep 27 2010

Fingerprint

Lewis Acids
Oximes
Cycloaddition
Estrone
Stereoselectivity
Nitrogen
Ions
Catalysts
nitrones
N-phenylmaleimide
estrone oxime
estrone 3-methyl ether

Keywords

  • Chemoselectivity
  • Cycloaddition
  • Nitrogen heterocycles
  • Stereoselectivity
  • Steroids

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Electrophile-and Lewis acid-induced nitrone formation and 1,3- dipolar cycloaddition reactions in the 13α- and 13β-estrone series. / Mernyák, E.; Huber, Judit; Benedek, Gabriella; Pfoh, Roland; Rühl, Stephan; Schneider, G.; Wölflinga, János.

In: Arkivoc, Vol. 2010, No. 11, 27.09.2010, p. 101-113.

Research output: Contribution to journalArticle

Mernyák, E. ; Huber, Judit ; Benedek, Gabriella ; Pfoh, Roland ; Rühl, Stephan ; Schneider, G. ; Wölflinga, János. / Electrophile-and Lewis acid-induced nitrone formation and 1,3- dipolar cycloaddition reactions in the 13α- and 13β-estrone series. In: Arkivoc. 2010 ; Vol. 2010, No. 11. pp. 101-113.
@article{788aa088764f4f98a470275c2035a031,
title = "Electrophile-and Lewis acid-induced nitrone formation and 1,3- dipolar cycloaddition reactions in the 13α- and 13β-estrone series",
abstract = "δ-Alkenyl oximes of 13a-estrone 3-methyl ether undergo intramolecular 1,3-dipolar cycloaddition reactions with BF3-OEt2 as catalyst, furnishing isoxazolidines. The reactions of the 13a- and 13β-estrone oximes with electrophiles lead to cyclic nitrones in high yields via attack of the oxime nitrogen on the intermediate halonium ions. In the intermolecular cycloadditions of 16-halomethyl nitrones to N-phenylmaleimide, single condensed aza-D-homo isoxazolidines are formed with high chemo- and stereoselectivity.",
keywords = "Chemoselectivity, Cycloaddition, Nitrogen heterocycles, Stereoselectivity, Steroids",
author = "E. Merny{\'a}k and Judit Huber and Gabriella Benedek and Roland Pfoh and Stephan R{\"u}hl and G. Schneider and J{\'a}nos W{\"o}lflinga",
year = "2010",
month = "9",
day = "27",
language = "English",
volume = "2010",
pages = "101--113",
journal = "Arkivoc",
issn = "1551-7012",
publisher = "Arkat USA",
number = "11",

}

TY - JOUR

T1 - Electrophile-and Lewis acid-induced nitrone formation and 1,3- dipolar cycloaddition reactions in the 13α- and 13β-estrone series

AU - Mernyák, E.

AU - Huber, Judit

AU - Benedek, Gabriella

AU - Pfoh, Roland

AU - Rühl, Stephan

AU - Schneider, G.

AU - Wölflinga, János

PY - 2010/9/27

Y1 - 2010/9/27

N2 - δ-Alkenyl oximes of 13a-estrone 3-methyl ether undergo intramolecular 1,3-dipolar cycloaddition reactions with BF3-OEt2 as catalyst, furnishing isoxazolidines. The reactions of the 13a- and 13β-estrone oximes with electrophiles lead to cyclic nitrones in high yields via attack of the oxime nitrogen on the intermediate halonium ions. In the intermolecular cycloadditions of 16-halomethyl nitrones to N-phenylmaleimide, single condensed aza-D-homo isoxazolidines are formed with high chemo- and stereoselectivity.

AB - δ-Alkenyl oximes of 13a-estrone 3-methyl ether undergo intramolecular 1,3-dipolar cycloaddition reactions with BF3-OEt2 as catalyst, furnishing isoxazolidines. The reactions of the 13a- and 13β-estrone oximes with electrophiles lead to cyclic nitrones in high yields via attack of the oxime nitrogen on the intermediate halonium ions. In the intermolecular cycloadditions of 16-halomethyl nitrones to N-phenylmaleimide, single condensed aza-D-homo isoxazolidines are formed with high chemo- and stereoselectivity.

KW - Chemoselectivity

KW - Cycloaddition

KW - Nitrogen heterocycles

KW - Stereoselectivity

KW - Steroids

UR - http://www.scopus.com/inward/record.url?scp=77958586784&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77958586784&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:77958586784

VL - 2010

SP - 101

EP - 113

JO - Arkivoc

JF - Arkivoc

SN - 1551-7012

IS - 11

ER -