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Practical Asymmetric Diels-Alder Additions to Camphor-10-sulfonic-Acid-Derived Acrylates. Preliminary Communication

✍ Scribed by Wolfgang Oppolzer; Christian Chapuis; Martha J. Kelly

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
205 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Starting from (+)‐camphor‐10‐sulfonic acid (1) the chiral crystalline alcohols 3 and 11 were prepared in two steps. Lewis‐acid‐mediated [4+2]‐additions of their acrylates to 1,3‐dienes were studied. Notably, the crystalline acrylate 4 underwent TiCl~2~ (OiPr)~2~‐promoted Diels‐Alder addition to cyclopentadiene giving after recrystallization efficiently the pure (2__R__)‐adduct 5.

📜 SIMILAR VOLUMES

Asymmetric induction in Diels-Alder reac
Asymmetric induction in Diels-Alder reactions to acrylates derived from chiral sec-alcohols. Preliminary communication
✍ Wolfgang Oppolzer; Mark Kurth; Daniel Reichlin; Christian Chapuis; Martin Mohnha 📂 Article 📅 1981 🏛 John Wiley and Sons 🌐 German ⚖ 328 KB

## Abstract Starting from the enantiomerically pure monoterpenes (+)‐pulegone (**3**), (+)‐limonene (**7**), (−)‐β‐pinene (**9**), (+)‐ and (−)‐camphor (**13**) or (+)‐cholestenone (**11**) the chiral alcohols **4, 5, 6, 8, 10, 12, 14, 15, 16, 17** et **18** were prepared; their acrylates **II** un

Camphor-Derived N-Acryloyl and N-Crotono
Camphor-Derived N-Acryloyl and N-Crotonoyl Sultams: Practical Activated Dienophiles in Asymmetric Diels-alder Reactions. Preliminary Communication
✍ Wolfgang Oppolzer; Christian Chapuis; Gérald Bernardinelli 📂 Article 📅 1984 🏛 John Wiley and Sons 🌐 German ⚖ 292 KB

## Abstract Starting from (+)‐camphor‐10‐sulfonyl chloride (**5**), the crystalline sultam **8** was easily prepared. __Lewis__‐acid‐promoted __Diels‐Alder__ additions of the crystalline __N__‐acry‐loyl and __N__‐crotonoyl derivatives **9** and __10__, respectively, to cyclopentadiene and 1,3‐butad