π-π Chelation controlled chemoselective conjugate addition of lithium dimethylcuprate

Naoki Asao, Sunyoung Lee, Yoshinori Yamamoto

    Research output: Contribution to journalArticlepeer-review

    3 Citations (Scopus)

    Abstract

    The conjugate addition of Me2CuLi to ethyl cinnamate derivatives bearing an alkynyl group at the ortho-position, took place preferentially in the presence of the corresponding α,β-unsaturated esters bearing an alkynyl group at the distal position or having no alkynyl groups. The observed chemoselectivity is most probably a reflection of the π-π chelation between π-electrons of the olefinic moiety of the enoates and those of the C-C triple bond located at the proximal position.

    Original languageEnglish
    Pages (from-to)1803-1805
    Number of pages3
    JournalTetrahedron Letters
    Volume44
    Issue number9
    DOIs
    Publication statusPublished - 2003 Feb 24

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

    Fingerprint Dive into the research topics of 'π-π Chelation controlled chemoselective conjugate addition of lithium dimethylcuprate'. Together they form a unique fingerprint.

    Cite this