Asymmetric Diels-Alder Reactions of Chiral N-Methacryloylsultams with 1,3-Dienes

Von Oppolzer, Wolfgang; Seletsky, Boris; Bernardinelli, Gérald Hugues

doi:10.1016/S0040-4039(00)73222-9

Scientific article

Letter

English

Asymmetric Diels-Alder Reactions of Chiral N-Methacryloylsultams with 1,3-Dienes

ContributorsVon Oppolzer, Wolfgang; Seletsky, Boris; Bernardinelli, Gérald Hugues

Published inTetrahedron Letters, vol. 35, no. 21, p. 3509-3512

Publication date1994

Abstract

R₂AlCl-coordinated N-methacryloylsultam 1c undergoes efficient, endo-selective and highly diastereoface controlled [4+2]-additions to cyclopentadiene, isoprene, (E)-piperylene and the 2-silyloxydienes 10 and 12. The resulting crystalline cycloadducts are smoothly reduced with LiAlH4 providing the recovered auxiliary and the corresponding enantiomerically pure alcohols.

Affiliation entities

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

Citation (ISO format)

VON OPPOLZER, Wolfgang, SELETSKY, Boris, BERNARDINELLI, Gérald Hugues. Asymmetric Diels-Alder Reactions of Chiral N-Methacryloylsultams with 1,3-Dienes. In: Tetrahedron Letters, 1994, vol. 35, n° 21, p. 3509–3512. doi: 10.1016/S0040-4039(00)73222-9

Article (Published version)

Identifiers

PID : unige:151912
DOI : 10.1016/S0040-4039(00)73222-9

Commercial URLhttps://linkinghub.elsevier.com/retrieve/pii/S0040403900732229

ISSN of the journal0040-4039

121views

16downloads

Creation20/05/2021 12:28:00

First validation20/05/2021 12:28:00

Update time16/03/2023 00:39:33

Status update16/03/2023 00:39:32

Last indexation02/10/2024 08:01:07

Archive ouverte UNIGE

Asymmetric Diels-Alder Reactions of Chiral N-Methacryloylsultams with 1,3-Dienes

Technical informations