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

Benedikt Skrobo, Jörg-Martin Neudörfl, Nils E. Schlörer, Jan Deska

Research output: Contribution to journalArticleScientificpeer-review

4 Citations (Scopus)
213 Downloads (Pure)

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

Keywords

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

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