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Preparation, structure and asymmetric diels-alder reactions of 10-arylsulfonylisobornyl acrylates

✍ Scribed by Wolfgang Oppolzer; Martha J. Kelly; Gérald Bernardinelli

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
216 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis

The crystalline chiral auxiliaries 4 and 5 were readily prepared from camphorsulfonic acid. Their acrylates underwent the Diels-Alder reactions 5 + 7 with modest asymmetric induction consistent with an X-ray study of k.

📜 SIMILAR VOLUMES

Asymmetric diels-alder reactions of acry
Asymmetric diels-alder reactions of acrylates derived from 3-alkyl-borneols and -isoborneols
✍ Wolfgang Oppolzer; Christian Chapuis 📂 Article 📅 1984 🏛 Elsevier Science 🌐 French ⚖ 177 KB

Starting from (+)-camphor the chiral alcohols 1 and 8 have been prepared; their acrylates 9 and 13 underwent TiC12(0iPr) -mediated Diels-Alder additions to cyclopentadiene zth stereoface-differen 3, iations of 66% d.e. and 94% d.e., respectively.

Practical Asymmetric Diels-Alder Additio
Practical Asymmetric Diels-Alder Additions to Camphor-10-sulfonic-Acid-Derived Acrylates. Preliminary Communication
✍ Wolfgang Oppolzer; Christian Chapuis; Martha J. Kelly 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 205 KB

## 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~‐prom