𝔖 Bobbio Scriptorium
✦   LIBER   ✦

High asymmetric induction in diels-alder additions of cyclopentadiene to acrylates derived from isoborneol

✍ Scribed by Wolfgang Oppolzer; Christian Chapuis; Guo Mao Dao; Daniel Reichlin; Thierry Godel

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
263 KB
Volume
23
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Starting from (R)-(+)-and from (S)-(-)-camphor the chiral alcohols 1: 2 and 3 have been prepared; their acrylates II underwent TiCl,(OR),-promoted Diels-Alder additTons to cyclopentadiene giving efficiently in a predictable manner either the (2R)-or the (2S)-adducts III with up to virtually quantitative asymmetric induction. The Diels-Alder addition of 1,3-dienes to olefins is a reaction of pre-eminent importance in organic synthesis. Consequently, considerable efforts have been expended to enantioselective versions of this process which may create two pairs of new chiral centers at the binding sites. Despite encouraging progress in this field, employing either chiral dienophiles', dienes2 or Lewis acid catalysts3, much remains to be done. Recently a host of .&-face directing acrylates A, E and C (Scheme 1) and their re-face directing counterparts have been added to cyclopentadiene in the presence of TiC14 with s90% predictable enantioselectionll.

πŸ“œ 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 πŸ“‚ Article πŸ“… 1984 πŸ› Elsevier Science 🌐 French βš– 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.

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 πŸ“‚ Article πŸ“… 1981 πŸ› John Wiley and Sons 🌐 German βš– 328 KB

## Abstract Starting from the enantiomerically pure monoterpenes (+)‐pulegone (**3**), (+)‐limonene (**7**), (βˆ’)‐β‐pinene (**9**), (+)‐ and (βˆ’)‐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

Organic reactions at high pressure. Asym
Organic reactions at high pressure. Asymmetric induction in the diels-alder reaction of p-benzoquinone with chiral 2,4-pentadienoic acid derivatives
✍ William G Dauben; Richard A Bunce πŸ“‚ Article πŸ“… 1982 πŸ› Elsevier Science 🌐 French βš– 209 KB

Asymmetric induction in the high pressure (15 kbar, 1.5 GPa) Duels-Alder reactlon of e-benzoqulnone with choral 2,4-pentadienoic acid derivatives is evaluated The reactions afford 4a,5,8,8a-tetrahydro-1,4-naphthalenedlones in up to 50% enantlomenc excess.