Highly Diastereoselective Desymmetrisation of Cyclic meso-Anhydrides and Derivatisation to Mono-Protected 1,4-Diols

Amanda C. Evans; Deborah A. Longbottom; Masato Matsuoka; Steven V. Ley

doi:10.1055/s-2005-862393

LETTER

Highly Diastereoselective Desymmetrisation of Cyclic meso-Anhydrides and Derivatisation to Mono-Protected 1,4-Diols

Amanda C. Evans^a, Deborah A. Longbottom^a, Masato Matsuoka^b, Steven V. Ley*^a
^a University of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, CB2 1EW, UK
Fax: +44(1223)336442; e-Mail: svl1000@cam.ac.uk;
^b Nippon Shinyaku Co., Ltd., 3-14-1 Sakura, Tsukuba, Ibaraki 305-0003, Japan

Abstract

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Abstract

A new and efficient desymmetrisation of bi- and tricyclic meso-anhydrides is described, providing good yields and diastereoselectivities in all cases (routinely >95% de). Derivatisation of the chiral compounds synthesised is then demonstrated by their conversion into mono-protected 1,4-diols.

Key words

chiral auxiliary - diastereoselectivity - desymmetrisation - stereoselective synthesis - anhydride

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References

For some general overviews of enantioselective desymmetrisation, please see:

1a Willis MC. J. Chem. Soc., Perkin Trans. 1 2001, 1765

1b Spivey AC. Andrews BI. Angew. Chem. Int. Ed. 2001, 40: 3131

1c Chen Y. McDaid P. Deng L. Chem. Rev. 2003, 103: 2965

1d Hoffman RW. Angew. Chem. Int. Ed. 2003, 42: 1096

For some examples of anhydride desymmetrisation as applied to total synthesis, please see:

2a Hashimato K. Kitaguchi J. Mizuno Y. Kobayashi T. Shirahama H. Tetrahedron Lett. 1996, 37: 2275

2b Hibbs DE. Hursthouse MB. Jones IG. Jones W. Abdul Malik KM. North M. Tetrahedron 1997, 53: 17417

2c Jones IG. Jones W. North M. Tetrahedron 1999, 55: 279

2d Verma R. Ghosh SK. J. Chem. Soc., Perkin Trans. 1 1999, 265

2e Starr JT. Koch G. Carreira EM. J. Am. Chem. Soc. 2000, 122: 8793

2f Choi C. Tian S.-K. Deng L. Synthesis 2001, 1737

2g Mittendorf J. Benet-Buchholz J. Fey P. Mohrs K.-H. Synthesis 2003, 1: 136

2h Hubbard RD. Miller BL. Tetrahedron 2003, 59: 8143

2i Mans DM. Pearson WH. Org. Lett. 2004, 6: 3305

3a Abiko A. Chem. Lett. 1995, 357

3b Abiko A. Moriya O. Filla SA. Masamune S. Angew. Chem., Int. Ed. Engl. 1995, 34: 793

3c Abiko A. Davis WM. Masamune S. Tetrahedron: Asymmetry 1995, 6: 1295

3d Abiko A. Masamune S. Tetrahedron Lett. 1996, 37: 1081

3e Abiko A. Heterogen. Chem. Rev. 1997, 17: 51

3f Abiko A. Masamune S. Tetrahedron Lett. 1997, 38: 3261

4 White JM. Tunoori AR. Georg GI. J. Am. Chem. Soc. 2000, 122: 11995