Highly stereoselective intermolecular oxy-michael addition reaction to α,β-unsaturated malonate esters

David J. Buchanan, Darren J. Dixon, Felix A. Hernandez-Juan

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The highly diastereoselective oxy-Michael addition of the "naked" anion of (6S)-methyl δ lactol to alkylidiene-, arylidene-, and heteroarylidene-malonate derivatives leading to the direct formation of THP*-protected β-hydroxy ester derivatives is described. Subsequent acid-mediated deprotection affords the enantioenriched aldol products in quantitative yields.
    Original languageEnglish
    Pages (from-to)1357-1360
    Number of pages3
    JournalOrganic Letters
    Volume6
    Issue number9
    DOIs
    Publication statusPublished - 29 Apr 2004

    Keywords

    • Crystal structure; Molecular structure (of (methyltetrahydropyranyloxy)hydroxymethyl(methyl)pentanol); Asymmetric synthesis and induction (stereoselective prepn. of (methyltetrahydropyranyloxy)alkanoates via stereoselective Michael addn. of methyltetrahydropyranol to alkylidene- or arylidenemalonates); Michael reaction (stereoselective; stereoselective prepn. of (methyltetrahydropyranyloxy)alkanoates via stereoselective Michael addn. of methyltetrahydropyranol to alkylidene- or arylidenemalonates); Esters Role: RCT (Reactant), RACT (Reactant or reagent) (a,b-unsatd.; stereoselective prepn. of (methyltetrahydropyranyloxy)alkanoates via stereoselective Michael addn. of methyltetrahydropyranol to alkylidene- or arylidenemalonates)

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