Kirmse–Doyle‐ and Stevens‐Type Rearrangements of Glutarate‐Derived Oxonium Ylides

Research output: Contribution to journalArticleScientificpeer-review

Researchers

Research units

  • University of Cologne

Abstract

A novel chemoenzymatic synthetic cascade enables the preparation of densely decorated tetrahydrofuran building blocks. Here, the lipase‐catalyzed desymmetrization of 3‐alkoxyglutarates renders highly enantioenriched carboxylic acid intermediates, whose subsequent activation and oxonium ylide rearrangement by means of rhodium or copper complexes furnishes functionalized O‐heterocycles with excellent diastereoselectivity. The two‐step protocol offers a streamlined and flexible synthesis of tetrahydrofuranones bearing different benzylic, allylic or allenylic side chains with full control over multiple stereogenic centers.

Details

Original languageEnglish
Pages (from-to)3209-3217
Number of pages9
JournalCHEMISTRY: A EUROPEAN JOURNAL
Volume24
Issue number13
Publication statusPublished - 2 Mar 2018
MoE publication typeA1 Journal article-refereed

    Research areas

  • transition metal catalysis, sigmatropic, lipase, heterocycles, chemoenzymatic

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