Simple Oxazolidine Chiral Diene Ligands for Enantioselective Rh-Catalyzed Conjugate Additions

Nathan W. G. Fairhurst; Rachel H. Munday; David R. Carbery

doi:10.1055/s-0032-1318135

Synlett, Inhaltsverzeichnis

Synlett 2013; 24(4): 496-498
DOI: 10.1055/s-0032-1318135

letter

Simple Oxazolidine Chiral Diene Ligands for Enantioselective Rh-Catalyzed Conjugate Additions

Nathan W. G. Fairhurst

^aDepartment of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK Fax: +44(1225)386231 eMail: d.carbery@bath.ac.uk

,

Rachel H. Munday

^bAstraZeneca, Pharmaceutical Development, Silk Road Business Park, Charter Way, Macclesfield, Cheshire, SK10 2NA, UK

,

David R. Carbery*

^aDepartment of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK Fax: +44(1225)386231 eMail: d.carbery@bath.ac.uk

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Abstract

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Abstract

Simple oxazolidine-based chiral diene ligands, ultimately derived from serine, have been synthesized using the Seebach self-regeneration of stereocenters strategy. The ligands have been used in the enantioselective Rh-catalyzed conjugate addition of aryl boronic acids to cyclohexenone. An efficient ‘in vacuo’ reaction protocol has been developed as part of this study.

Key words

dienes - chirality - enantioselectivity - rhodium - oxazolidines

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Referenzen

References and Notes

For relevant reviews of chiral dienes and seminal reports of enantioselective Rh-catalyzed conjugate addition of boronic acids, see:

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