Asymmetric synthesis of a β-lactam framework via the conjugate addition of amidocuprates(I) to chiral enoates

Naoki Asao, T. Uyehara, N. Tsukada, Y. Yamamoto

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    8 Citations (Scopus)

    Abstract

    Amidocuprate(I) reagents {Li[Cu(NR2)2]} and higher order cyanocuprates(I) {Li2[Cu(CN)(NR2)2]} have been developed as a new class of nitrogen nucleophiles. These reagents underwent regioselective 1,4-additions to α,β:γ,δ-dienoates, whereas NHR2 gave a 1,6-addition product and the lithium reagent LiNR2 afforded a mixture of 1,4- and 1,2-addition products. The amidocuprates(I) were added to chiral α,β:γ,δ-dienones having a 8-phenyl-p-menth-3-yl or a 10,2-bornanesultam chiral auxiliary in order to produce 1,4-adducts in good to high diastereoselectivity. The addition of Li[Cu{N(Bn)(TMS)}2] and Li2[Cu(CN){N(Bn)(TMS)}2] to 8-phenyl-p-menth-3-yl 5-phenyl-2,4-pentadienoate or N-(5-phenyl-2,4-pentadienoyl)-10,2-bornanesultam produced an (R)-chirality at the β-position. The 1,4-addition of Li2[Cu(CN){N(Bn)(TMS)}2] to the bornanesultam, followed by trapping with acetaldehyde, gave the α-(1-hydroxyethyl)-β-amino derivative as a single isomer in good yield. This three-component coupling was used in an asymmetric synthesis of a β-lactam.

    Original languageEnglish
    Pages (from-to)2103-2111
    Number of pages9
    JournalBulletin of the Chemical Society of Japan
    Volume68
    Issue number8
    DOIs
    Publication statusPublished - 1995 Aug 1

    ASJC Scopus subject areas

    • Chemistry(all)

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