Synthesis of 1,3-Diols by O-Nucleophile Additions to Activated Alkenes

Diego Gamba-Sánchez; Joëlle Prunet

doi:10.1055/s-0037-1610248

Synthesis, Table of Contents

Synthesis 2018; 50(20): 3997-4007
DOI: 10.1055/s-0037-1610248

short review

Synthesis of 1,3-Diols by O-Nucleophile Additions to Activated Alkenes

Diego Gamba-Sánchez

^aLaboratory of Organic Synthesis, Bio and Organocatalysis, Chemistry Department, Universidad de los Andes, Cra 1 No. 18A-12 Q:305, Bogotá 111711, Colombia Email: da.gamba1361@uniandes.edu.co

,

Joëlle Prunet

^bWestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ, UK Email: joelle.prunet@glasgow.ac.uk

› Author Affiliations

Abstract

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Abstract

The diastereoselective synthesis of 1,3-diols by addition of oxygen nucleophiles to activated alkenes is presented. This review focuses on homoallylic alcohol substrates that react with a relay compound to form an intermediate oxygen nucleophile, which in turn will lead to a protected 1,3-diol by intramolecular addition to the olefin moiety.

1 Introduction

2 Base Catalysis

3 Organocatalysis

4 Activation with Non-Metallic Electrophiles

5 Activation with Transition Metal Derivatives

6 Conclusions

Key words

1,3-diols - oxa-Michael - oxygen nucleophiles - activated alkenes - Tsuji–Trost reaction

Full Text

References

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