𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Search for ideal sulfinyl dienophile and dipolarophile

✍ Scribed by José L. García Ruano; Ana M. Martín Castro; Jesús H. Rodríguez Ramos

Book ID
102230823
Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
306 KB
Volume
13
Category
Article
ISSN
1042-7163

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

By analysis, the advantages and drawbacks of the differently substituted vinyl sulfoxides so far reported, (Z)‐3‐p‐tolylsulfinyl acrylonitriles are proposed as the best sulfinyl dienophiles. The stereoselective synthesis of these compounds was optimized by hydrocyanation of sulfinyl alkynes with Et~2~AlCN. Their behavior as chiral dienophiles and dipolarophiles is responsible for the high stereocontrol of Diels–Alder and 1,3‐dipolar reactions, respectively. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:453–462, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10066

📜 SIMILAR VOLUMES

Preparation and evaluation of N-sulfinyl
Preparation and evaluation of N-sulfinyl dienophiles for asymmetric hetero-diels-alder reactions
✍ Molla Mellese Endeshaw; Lars K. Hansen; Odd R. Gautun 📂 Article 📅 2008 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 812 KB

## Abstract magnified image A series of __N__‐sulfinyl dienophiles **1c‐i** has been screened in asymmetric hetero‐Diels‐Alder reactions using chiral bis(oxazoline)copper(II) and ‐zinc(II) triflates. The survey pointed out __N__‐sulfine **1c** (R  P(O)(OPh)~2~) as the most promising __N__‐sulfin