Evaluation of a Pseudoephedrine Linker for Asymmetric Alkylations on Solid Phase

Panee C. Hutchison, Tom D. Heightman, David J. Procter

    Research output: Contribution to journalArticlepeer-review

    Abstract

    (Equation Presented) Immobilized pseudoephedrine amides have been conveniently prepared by attachment of pseudoephedrine to Merrifield resin and acylation on nitrogen. Deprotonation and alkylation of the resin bound amides proceeds smoothly. Products were cleaved from the resin to give ketones and alcohols in high enantiomeric excess and moderate to good overall yield.
    Original languageEnglish
    Pages (from-to)4583-4585
    Number of pages2
    JournalOrganic Letters
    Volume4
    Issue number26
    DOIs
    Publication statusPublished - 26 Dec 2002

    Keywords

    • Chiral auxiliary (enantioselective prepn. of primary alcs. and ketones using enantioselective alkylation of amides contg. a resin-bound pseudoephedrine auxiliary as the key step); Asymmetric synthesis and induction; Solid phase synthesis (enantioselective prepn. of primary alcs. and ketones using enantioselective alkylation of resin-bound pseudoephedrine amides as the key step); Ketones Role: SPN (Synthetic preparation), PREP (Preparation) (enantioselective prepn. of primary alcs. and ketones using enantioselective alkylation of resin-bound pseudoephedrine amides as the key step); Alcohols Role: SPN (Synthetic preparation), PREP (Preparation) (primary; enantioselective prepn. of primary alcs. and ketones using enantioselective alkylation of resin-bound pseudoephedrine amides as the key step); Alkylation (stereoselective; enantioselective prepn. of primary alcs. and ketones using enantioselective alkylation of resin-bound pseudoephedrine amides as the key step)

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