Asymmetric Diels-Alder reactions of acrylates derived from 3-alkyl-borneols and -isoborneols

Von Oppolzer, Wolfgang; Chapuis, Christian

doi:10.1016/S0040-4039(01)91290-0

Scientific article

Letter

English

Asymmetric Diels-Alder reactions of acrylates derived from 3-alkyl-borneols and -isoborneols

ContributorsVon Oppolzer, Wolfgang; Chapuis, Christian

Published inTetrahedron letters, vol. 25, no. 47, p. 5383-5386

Publication date1984

Abstract

Starting from (+)-camphor the chiral alcohols 7 and 8 have been prepared; their acrylates 9 and 13 underwent TiCl₂(OiPr)₂-mediated Diels-Alder addition to cyclopentadiene with stereoface-differentiations of 66% d.e. and 94% d.e., respectively.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON OPPOLZER, Wolfgang, CHAPUIS, Christian. Asymmetric Diels-Alder reactions of acrylates derived from 3-alkyl-borneols and -isoborneols. In: Tetrahedron letters, 1984, vol. 25, n° 47, p. 5383–5386. doi: 10.1016/S0040-4039(01)91290-0

Article (Published version)

Identifiers

PID : unige:168003
DOI : 10.1016/S0040-4039(01)91290-0

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/S0040403901912900

Journal ISSN0040-4039

58views

0downloads

Creation05/04/2023 09:07:07

First validation05/04/2023 09:58:03

Update05/04/2023 09:58:03

Status update05/04/2023 09:58:03

Last indexation01/11/2024 04:42:57

Archive ouverte UNIGE

Asymmetric Diels-Alder reactions of acrylates derived from 3-alkyl-borneols and -isoborneols

Starting from (+)-camphor the chiral alcohols 7 and 8 have been prepared; their acrylates 9 and 13 underwent TiCl2(OiPr)2-mediated Diels-Alder addition to cyclopentadiene with stereoface-differentiations of 66% d.e. and 94% d.e., respectively.

Technical informations

Starting from (+)-camphor the chiral alcohols 7 and 8 have been prepared; their acrylates 9 and 13 underwent TiCl₂(OiPr)₂-mediated Diels-Alder addition to cyclopentadiene with stereoface-differentiations of 66% d.e. and 94% d.e., respectively.