Stereocontrolled Synthesis of Polypropionate Fragments based on a Building Block Assembly Strategy using Lithiation-Borylation Methodologies

Alba Millan Delgado, Pablo Grigol Martinez, Varinder Aggarwal

Research output: Contribution to journalArticle (Academic Journal)peer-review

9 Citations (Scopus)
287 Downloads (Pure)

Abstract

Polypropionates are important structural motifs in nature and are commonly made by iterative aldol or crotylation methodologies. Herein, an alternative strategy is presented in which stereochemically predefined building blocks, bearing appropriate functionality, are coupled together using a lithiation-borylation methodology with complete stereocontrol. The building blocks comprise lithiated carbamates acting as donors, and boronic esters acting as acceptors. The acceptor building blocks contain β-hydroxyl groups masked as silyl groups to avoid elimination of the boronate intermediates. Subsequent oxidation of both the boron and silyl moieties can then deliver an array of polypropionate fragments with full stereochemical control, including the synthetically challenging anti-anti isomers.

Original languageEnglish
Pages (from-to)730-735
Number of pages6
JournalChemistry - A European Journal
Volume24
Issue number3
Early online date11 Dec 2017
DOIs
Publication statusPublished - 12 Jan 2018

Keywords

  • diastereoselectivity
  • lithiation-borylation
  • polypropionate
  • silaboration
  • stereo-n-ads

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