Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation to mono-protected 1,4-diols

Synlett

Volumn , Issue 4, 2005, Pages 646-648

  Evans, Amanda C ^a   Longbottom, Deborah A ^a   Matsuoka, Masato ^b   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b NIPPON SHINYAKU CO LTD   (Japan)

Author keywords

Anhydride; Chiral auxiliary; Desymmetrisation; Diastereoselectivity; Stereoselective synthesis

Indexed keywords

ACID ANHYDRIDE; BICYCLO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; DERIVATIZATION; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 15444378959     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-862393     Document Type: Article

References (20)

1. For some general overviews of enantioselective desymmetrisation, please see: (a) Willis, M. C. J. Chem. Soc., Perkin Trans, 1 2001, 1765.
2. (b) Spivey, A. C.; Andrews, B. I. Angew. Chem. Int. Ed. 2001, 40, 3131.
3. (c) Chen, Y.; McDaid, P.; Deng, L. Chem. Rev. 2003, 103, 2965.
4. (d) Hoffman, R. W. Angew. Chem. Int. Ed. 2003, 42, 1096.
5. For some examples of anhydride desymmetrisation as applied to total synthesis, please see: (a) Hashimato, K.; Kitaguchi, J.; Mizuno, Y.; Kobayashi, T.; Shirahama, H. Tetrahedron Lett. 1996, 37, 2275.
6. (b) Hibbs, D. E.; Hursthouse, M. B.; Jones, I. G.; Jones, W.; Abdul Malik, K. M.; North, M. Tetrahedron 1997, 53, 17417.
7. (c) Jones, I. G.; Jones, W.; North, M. Tetrahedron 1999, 55, 279.
8. (d) Verma, R.; Ghosh, S. K. J. Chem. Soc., Perkin Trans, 1 1999, 265.
9. (e) Starr, J. T.; Koch, G.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 8793.
10. (f) Choi, C.; Tian, S.-K.; Deng, L. Synthesis 2001, 1737.
11. (g) Mittendorf, J.; Benet-Buchholz, J.; Fey, R; Mohrs, K.-H. Synthesis 2003, 1, 136.
12. (h) Hubbard, R. D.; Miller, B. L. Tetrahedron 2003, 59, 8143.
13. (i) Mans, D. M.; Pearson, W. H. Org. Lett. 2004, 6, 3305.
14. (a) Abiko, A. Chem. Lett. 1995, 357.
15. (b) Abiko, A.; Moriya, O.; Filla, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 793.
16. (c) Abiko, A.; Davis, W. M.; Masamune, S. Tetrahedron: Asymmetry 1995, 6, 1295.
17. (d) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1081.
18. (e) Abiko, A. Heterogen. Chem. Rev. 1997, 17, 51.
19. (f) Abiko, A.; Masamune, S. Tetrahedron Lett. 1997, 38, 3261.
20. White, J. M.; Tunoori, A. R.; Georg, G. I. J. Am. Chem. Soc. 2000, 122, 11995.