Migratory Dynamic Kinetic Resolution of Carbocyclic Allylic Alcohols

Chicco Manzuna Sapu, Tamas Görbe, Richard Lihammar, Jan-E. Bäckvall, Jan Deska

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Abstract

A novel migratory dynamic kinetic resolution based on the interplay between an enzyme acylation catalyst and a heterogeneous Bronsted acid as an isomerization/racemization catalyst gives rise to carbocyclic allylic esters with excellent stereoselectivity from readily available tertiary carbinols. An easy-to-use teabag setup combining resin-bound catalysts, a biphasic isooctanewater solvent system, and a highly lipophilic acyl donor efficiently suppresses side reactions and allows for the preparation of functionalized carbocyclic building blocks in high yields and optical purity.

Original languageEnglish
Pages (from-to)5952-5955
Number of pages4
JournalORGANIC LETTERS
Volume16
Issue number22
DOIs
Publication statusPublished - 21 Nov 2014
MoE publication typeA1 Journal article-refereed

Keywords

  • TERTIARY ALCOHOLS
  • CATALYSIS
  • DESYMMETRIZATION
  • REARRANGEMENT

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