Scalable synthesis of enantiomerically pure syn -2,3-dihydroxybutyrate by sharpless asymmetric dihydroxylation of p -phenylbenzyl crotonate

Journal of Organic Chemistry

Volumn 76, Issue 20, 2011, Pages 8554-8559

  Smaltz, Daniel J ^a   Myers, Andrew G ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC DIHYDROXYLATION; CHIRAL BUILDING BLOCKS; EFFICIENT RECYCLING; ENANTIO; SCALABLE SYNTHESIS; SYNTHETIC ROUTES;

4 PHENYLBENZYL CROTONATE; BENZYL ALCOHOL DERIVATIVE; BUTYRIC ACID DERIVATIVE; CROTONIC ACID DERIVATIVE; DIHYDROXYBUTYRIC ACID ACETONIDE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CRYSTALLIZATION; DIHYDROXYLATION; ENANTIOMER; SYNTHESIS;

ALCOHOLS; CHEMISTRY, ORGANIC; CROTONATES; CRYSTALLIZATION; HYDROXYBUTYRATES; HYDROXYLATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHENOLS; RECYCLING; STEREOISOMERISM;

EID: 80054100632     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2016746     Document Type: Article

References (30)

1. Roush, W. R.; Lin, X.; Straub, J. A. J. Org. Chem. 1991, 56, 1649-1655
2. Ruiz, M; Ojea, V; Quintela, J. M. Tetrahedron: Asymmetry 2002, 123, 1535-1549
3. Gardiner, J. M.; Panchal, N. R.; Stimpson, W. T.; Herbert, J. M.; Ellames, G. J. Synlett 2005, 2685-2687
4. Servi, S. J. Org. Chem. 1985, 50, 5867-5869
5. Oppolzer, W.; Barras, J.-P. Helv. Chim. Acta 1987, 70, 1666-1675
6. Dewanckele, J. M.; Röper, H. Tetrahedron Lett. 1989, 30, 5319-5322
7. Shirahata, K.; Iida, T.; Hirayama, N. Symp. Chem. Nat. Prod. 1981, 24, 199-206
8. Axenose, the deacetylated form of trioxacarcinose A, appears in members of the axenomycin class of natural products. See: Arcamone, F.; Barbieri, W.; Franceschi, G.; Penco, S.; Vigevani, A. J. Am. Chem. Soc. 1973, 95, 2008-2009
9. For a review of the Sharpless asymmetric dihydroxylation, see: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 2483-2547
10. Gardiner, J.; Panchal, N.; Stimpson, W.; Herbert, J.; Ellames, G. Synlett 2005, 17, 2685-2687
11. However, to the best of our knowledge, this substance is no longer widely available. For the preparation of 1 ethyl ester, see: Sakai, T.; Nakamura, T.; Fukuda, K.; Amano, E.; Utaka, M.; Takeda, A. Bull. Chem. Soc. Jpn. 1986, 59, 3185-3188
12. Bull, J. A.; Balskus, E. P.; Horan, R. A. J.; Langner, M.; Ley, S. V. Chem. Eur. J. 2007, 13, 5515-5538
13. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa, K.; Wang, Z. M.; Xu, D.; Zhang, X. L. J. Org. Chem. 1992, 57, 2768-2771
14. Kwong, H.-L.; Sorato, C.; Ogino, Y.; Chen, H.; Sharpless, K. B. Tetrahedron Lett. 1990, 31, 2999-3002
15. Wai, J. S. M.; Markó, I.; Svendsen, J. S.; Finn, M. G.; Jacobsen, E. N.; Sharpless, K. B. J. Am. Chem. Soc. 1989, 111, 1123-1125
16. 1H NMR analysis of the corresponding bis-Mosher ester. See: Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549
17. Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. 1996, 35, 448-451
18. This degree of enantioselectivity is in excellent agreement with a previous report: Tagami, K.; Takagi, S.; Shiro, M.; Nagao, Y. Heterocycles 1997, 45, 1663-1669
19. Mahalingam, S. M.; Sathyamurthi, N.; Aidhen, I. S. Adv. Synth. Catal. 2005, 347, 715-717
20. Umemura, E.; Tsuchiya, T.; Umezawa, S. J. Antibiot. 1988, 41, 530-537
21. Klein, U.; Mohrs, K.; Wild, H.; Steglich, W. Liebigs Ann. Chem. 1987, 485-489
22. Walsh, P. J.; Sharpless, K. B. Synlett 1993, 605-606
23. AD mix containing 5 mol % potassium osmate and 1 mol % PHAL ligand is referred to in the literature as modified-AD-mix. See: Bennani, Y. L.; Sharpless, K. B. Tetrahedron Lett. 1993, 34, 2079-2082
24. Roberts et al. have designed a Super-AD-mix containing 8-10 mol % osmium tetroxide and 10 mol % PHAL ligand: Hermitage, S. A.; Murphy, A.; Nielsen, P.; Roberts, S. M. Tetrahedron 1998, 54, 13185-13202
25. Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709
26. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818
27. Still, W. C.; Khan, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925
28. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520
29. A preparation of amide ent-4 is described, but characterization data were not reported: Ziegler, F.; Kim, H. Tetrahedron Lett. 1993, 34, 7669-7672
30. For characterization data for ent-5, see: Aoyagi, S.; Wang, T. C.; Kibayashi, C. J. Am. Chem. Soc. 1993, 115, 11393-11409