Diastereoselective synthesis of (1S,2S,3R,6S) 3-Chloro-3-methyl-6-isopropenyl-1,2-cyclohexanediol via Prins reaction induced by zinc and trimethylsilyl chloride

Marty, Maurus; Stoeckli-Evans, Helen; Neier, Reinhard

doi:10.1016/0040-4020(96)00167-6

Diastereoselective synthesis of (1S,2S,3R,6S) 3-Chloro-3-methyl-6-isopropenyl-1,2-cyclohexanediol via Prins reaction induced by zinc and trimethylsilyl chloride

Auteur(s)

Marty, Maurus

Stoeckli-Evans, Helen

Institut de physique

Neier, Reinhard

Institut de chimie

Date de parution

1996

In

Tetrahedron, Elsevier, 1996/52/13/4645-4658

Résumé

While attempting to synthesize a potential inhibitor of the biosynthetic step of formation of PBG, a novel catalytic system inducing the Prins reaction was discovered. Treatment of epoxy geranial with Zn and trimethylsilyl chloride gave (1S,2S,3R,6S) 3-Chloro-3-methyl-6-isopropenyl-1,2-cyclohexanediol in high diastereoselectivity.

Identifiants

https://libra.unine.ch/handle/123456789/17653

_

10.1016/0040-4020(96)00167-6

Type de publication

journal article

Dossier(s) à télécharger

main article: Marty_Maurus_-_Diastereoselective_synthesis_of_1S_2S_3R_6S_20070827.pdf (1020.59 KB)

google-scholar

Options

Diastereoselective synthesis of (1S,2S,3R,6S) 3-Chloro-3-methyl-6-isopropenyl-1,2-cyclohexanediol via Prins reaction induced by zinc and trimethylsilyl chloride