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, Table of Contents

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

letter

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

Authors

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

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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References

References and Notes

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

1a Shintani R, Hayashi T. Aldrichimica Acta 2009; 42: 31
1b Defieber C, Grützmacher H, Carreira EM. Angew. Chem. Int. Ed. 2008; 47: 4482
1c Glorius F. Angew. Chem. Int. Ed. 2004; 43: 3364
1d Sakai M, Hayashi H, Miyaura N. Organometallics 1997; 16: 4229
1e Takaya Y, Ogasawara M, Hayashi T, Sakai M, Miyaura T. J. Am. Chem. Soc. 1998; 120: 5579
1f Fischer C, Defieber C, Suzuki T, Carreira EM. J. Am. Chem. Soc. 2004; 126: 1628

2 Hayashi T, Ueyama K, Tokunaga N, Yoshida K. J. Am. Chem. Soc. 2003; 125: 11508
3 Defieber C, Paquin J.-F, Serna S, Carreira EM. Org. Lett. 2004; 6: 3873
4 Hu X, Zhuang M, Cao Z, Du H. Org. Lett. 2009; 11: 4744
5 Trost BM, Burns AC, Tautz T. Org. Lett. 2011; 13: 4566
6 Li Q, Dong Z, Yu Z.-X. Org. Lett. 2011; 13: 1122

7a Tellam JP, Kociok-Köhn G, Carbery DR. Org. Lett. 2008; 10: 5199
7b Tellam JP, Carbery DR. J. Org. Chem. 2010; 75: 7491
7c Tellam JP, Carbery DR. Tetrahedron Lett. 2011; 52: 6027

8a Ylioja PM, Mosley AD, Charlot CE, Carbery DR. Tetrahedron Lett. 2008; 49: 1111
8b Harker WR. R, Carswell EL, Carbery DR. Org. Lett. 2010; 12: 3712
8c Harker WR. R, Carswell EL, Carbery DR. Org. Biomol. Chem. 2012; 10: 1406
8d Heffernan SJ, Carbery DR. Tetrahedron Lett. 2012; 53: 5180

9 Fairhurst NW. G, Mahon MF, Munday RH, Carbery DR. Org. Lett. 2012; 14: 756
10 It is important to note that the cost ratio of d-serine to l-serine is only 2:1 based on current Sigma-Aldrich prices for comparable grades of product.
11 Di Giacomo M, Vinci V, Serra M, Colombo L. Tetrahedron: Asymmetry 2008; 19: 247
12 Methyallyl iodide prepared by Finkelstein reaction from the homolgous chloride, see: Baughman TW, Sworen JC, Wagener KB. Tetrahedron 2004; 60: 10943
13 Feng X, Wang Y, Wei B, Yang J, Du H. Org. Lett. 2011; 13: 3300

Supplementary Material

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