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Asymmetric induction in the 1,3-dipolar cycloaddition of chiral nitrile oxide derived from (2R)-bornane-10,2-sultam

✍ Scribed by Julita Jóźwik; Malgorzata Kosior; Jaroslaw Kiegiel; Janusz Jurczak

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
75 KB
Volume
13
Category
Article
ISSN
0899-0042

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✦ Synopsis

Abstract

The efficient preparation of the chiral nitrile oxide derived from N‐glyoxyloyl‐(2__R__)‐bornane‐10,2‐sultam is presented. The nitrile oxide was trapped in situ with substituted olefins as dipolarophiles to furnish optically active 2‐isoxazolines. Chirality 13:629–630, 2001. © 2001 Wiley‐Liss, Inc.

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1,3-Dipolar Cycloadditions of a 2-Oxoethanenitrile Oxide Derived from (2R)-Bornane-10,2-sultam to Electronically Modified 4,4′-Disubstituted Stilbenes
✍ Jan Romanski; Christian Chapuis; Janusz Jurczak 📂 Article 📅 2009 🏛 John Wiley and Sons 🌐 German ⚖ 362 KB

Thanks to its type-II dipole nature, we were able to demonstrate the higher reactivity of the SO 2 / C¼O syn-conformer for the uncatalyzed 1,3-dipolar cycloaddition of the 2-oxoethanenitrile oxide 2 derived from bornane-10,2-sultam to the symmetric 4,4'-disubstituted trans-stilbenes 3a -3i. The C(a)