A Convenient Route to Enantiomerically Pure 2-Substituted Methyl Glycerate Derivatives

Organic Letters

Volumn 5, Issue 24, 2003, Pages 4553-4555

  Ley, Steven V ^a   Michel, Patrick ^a   Trapella, Claudio ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; GLYCERALDEHYDE; GLYCERIC ACID; LITHIUM DERIVATIVE; METHYL GROUP;

ALKYLATION; ARTICLE; ENANTIOMER; STEREOCHEMISTRY;

ALKYLATION; CRYSTALLOGRAPHY, X-RAY; GLYCERALDEHYDE; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 0347411091     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035567+     Document Type: Article

References (22)

1. Total Synthesis of Natural Products: The "Chiron" Approach; Hanessian, S., Ed; Pergamon Press: Oxford, 1983.
2. (a) Barner, R.; Schmid, M. Helv. Chim. Acta 1979, 62, 2384.
3. (b) Dung, J.-S.; Armstrong, R. W.; Anderson, O. P.; Williams, R. M. J. Org. Chem. 1983, 48, 3592.
4. (b) Fors, K. S.; Gage, J. R.; Heier, R. F.; Kelly, R. C.; Perrault, W. R.; Wicnienski, N. J. Org. Chem. 1998, 63, 7348.
5. (c) Steinreiber, A.; Hellström, H.; Mayer, S. F.; Orru, R. V. A.; Faber, K. Synlett 2001, 111.
6. Harada, T.; Nakajima, H.; Ohnishi, T.; Takeuchi, M.; Oku, A. J. Org. Chem. 1992, 57, 720.
7. (a) Hosokawa, T.; Makabe, Y.; Shinohara, T.; Murahashi, S.-I. Chem. Lett. 1985, 1529.
8. (b) Tanner, D.; Somfai, P. Tetrahedron 1986, 42, 5985.
9. (a) Rodríguez. J. B.; Markey, S. P.; Ziffer, H. Tetrahedron: Asymmetry 1993, 4, 101.
10. (b) Avenoza, A.; Cativiela, C.; Peregrina, J. M.; Sucunza, D.; Zurbano, M. M. Tetrahedron: Asymmetry 2001, 12, 1383.
11. Genot, A.; Florent, J.-C; Monneret, C. J. Org. Chem. 1987, 52, 1057.
12. (a) Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194.
13. (b) Tse, B.; Blazey, C. M.; Tu, B.; Balkovec, J. J. Org. Chem. 1997, 62, 3236.
14. (c) Yen, K.-F.; Uang, B.-J. Tetrahedron: Asymmetry 1992, 3, 697.
15. Ley, S. V.; Baeschlin, D. K.; Dixon, D. J.; Foster, A. C.; Ince, S. J.; Priepke, W. M.; Reynolds, D. J. Chem. Rev. 2001, 101, 53. For a recent application, see: Diez E.; Dixon, D. J.; Ley, S. V.; Polara, A.; Rodriguez, F. Synlett 2003, 1186 and references therein.
16. Ley, S. V.; Baeschlin, D. K.; Dixon, D. J.; Foster, A. C.; Ince, S. J.; Priepke, W. M.; Reynolds, D. J. Chem. Rev. 2001, 101, 53. For a recent application, see: Diez E.; Dixon, D. J.; Ley, S. V.; Polara, A.; Rodriguez, F. Synlett 2003, 1186 and references therein.
17. (a) Michel, P.; Ley, S. V. Angew. Chem., Int. Ed. 2002, 41, 3898.
18. (b) Michel, P.; Ley, S. V. Synthesis 2003, 1598.
19. 6: C, 53.21; H, 8.12. Found: C, 53.15; H, 8.05.
20. Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447.
21. A 2:1 mixture at the secondary alcohol center was obtained when aldehydes were used as electrophiles. This reaction is still under investigation to improve the diastereoselectivity.
22. Ley, S. V.; Michel, P. Synlett 2001, 1793.