𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Asymmetric induction in the [4+2]cycloaddition of cyclopentadiene and furan to chiral derivatives of fumaric acid

✍ Scribed by Anna Kucharska; Renata Gorczyńska; Christian Chapuis; Janusz Jurczak

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

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

[4+2]Cycloaddition reactions of cyclopentadiene (1a) and furan (1b) to N,N′‐fumaroyldi[(2__R__)‐bornane‐10,2‐sultam] (2) and to N,N′‐fumaroyldi[(2__R__)‐bornane‐10,2‐(2′‐phenyl‐pyrazol‐3′‐one)] (3) are presented. A correlation between the solvent polarity and the logarithm of the diastereoisomer ratio (dr) was found for the uncatalyzed [4+2]cycloaddition of 1a to 3. Chirality 13:631–633, 2001. © 2001 Wiley‐Liss, Inc.

📜 SIMILAR VOLUMES

Stereoselectivity in the TiCl4-Catalyzed
Stereoselectivity in the TiCl4-Catalyzed [4+2] Cycloaddition of Cyclopentadiene to (2R)-Bornane-10,2-sultam Derivatives of Fumaric Acid Monoesters
✍ Michal Achmatowicz; Christian Chapuis; Piotr Rzepecki; Janusz Jurczak 📂 Article 📅 1999 🏛 John Wiley and Sons 🌐 German ⚖ 134 KB 👁 2 views

The [4 2] cycloaddition of cyclopentadiene to the (2R )-bornane-10,2-sultam derivative (À)-1b of fumaric monomethyl ester proceeds with high endo and p-facial diastereoselectivity in the presence of 0.5 mol-equiv. of TiCl 4 . The major diastereoisomer endo-(2R,3R )-2b, isolated in 87% yield by cryst

ChemInform Abstract: Asymmetrical [4 + 2
ChemInform Abstract: Asymmetrical [4 + 2]-Cycloaddition of (-)-Menthyl Acrylate and (-)-Menthyl Methacrylate to Cyclopentadiene in the Presence of BBr3.
✍ E. G. Mamedov 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

Asymmetric induction in the 1,3-dipolar
Asymmetric induction in the 1,3-dipolar cycloaddition of chiral nitrile oxide derived from (2R)-bornane-10,2-sultam
✍ Julita Jóźwik; Malgorzata Kosior; Jaroslaw Kiegiel; Janusz Jurczak 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 75 KB

## 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 Wile