Asymmetric Induction on Copper(I) Chloride Catalyzed 1,4-Addition of Alkylmagnesium Chlorides to α,β-Disubstituted (E)-Enoylsultams and Subsequent Protonation

Von Oppolzer, Wolfgang; Kingma, Arend Jouke

doi:10.1002/hlca.19890720622

Scientific article

English

Asymmetric Induction on Copper(I) Chloride Catalyzed 1,4-Addition of Alkylmagnesium Chlorides to α,β-Disubstituted (E)-Enoylsultams and Subsequent Protonation

ContributorsVon Oppolzer, Wolfgang; Kingma, Arend Jouke

Published inHelvetica Chimica Acta, vol. 72, no. 6, p. 1337-1345

Publication date1989

Abstract

Successive treatment of conjugated N-enoylsultams 2 with alkyl Grignard reagents/CuCl and aq. NH₄Cl solution generated selectively two stereogenic centers at C(α) and C(β) providing, after flash chromatography and crystallization, acylsultams 5 in high purity. Mild cleavage afforded the recovered sultam auxiliary 1 and enantiomerically pure carboxylic acids 7.

Affiliation entities

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

Citation (ISO format)

VON OPPOLZER, Wolfgang, KINGMA, Arend Jouke. Asymmetric Induction on Copper(I) Chloride Catalyzed 1,4-Addition of Alkylmagnesium Chlorides to α,β-Disubstituted (E)-Enoylsultams and Subsequent Protonation. In: Helvetica Chimica Acta, 1989, vol. 72, n° 6, p. 1337–1345. doi: 10.1002/hlca.19890720622

Article (Published version)

Identifiers

PID : unige:152892
DOI : 10.1002/hlca.19890720622

Commercial URLhttps://onlinelibrary.wiley.com/doi/10.1002/hlca.19890720622

ISSN of the journal0018-019X

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Asymmetric Induction on Copper(I) Chloride Catalyzed 1,4-Addition of Alkylmagnesium Chlorides to α,β-Disubstituted (E)-Enoylsultams and Subsequent Protonation

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