Development of ProPhenol ligands for the diastereo- and enantioselective synthesis of β-hydroxy-α-amino esters

Journal of the American Chemical Society

Volumn 136, Issue 8, 2014, Pages 3016-3019

  Trost, Barry M ^a   Miege, Frédéric ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ESTER; LIGAND; PHENOL DERIVATIVE; SCHIFF BASE; ZINC;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; CATALYSIS; ESTERS; LIGANDS; MOLECULAR STRUCTURE; PHENOLS; SCHIFF BASES; STEREOISOMERISM; ZINC;

EID: 84894620752     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4129394     Document Type: Article

References (30)

1. For a review on vancomycin and other related glycopeptides, see: Boger, D. L. Med. Res. Rev. 2001, 21, 356-381
2. Miller, M. J. Acc. Chem. Res. 1986, 19, 49-56
3. Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619
4. For a review on β-hydroxy-α-amino acids, see: Makino, K.; Hamada, Y. J. Synth. Org. Chem. Jpn. 2005, 63, 1198-1208
5. Aldolases, such as serine hydroxymethyltransferase (SHMT) and threonine aldolase (ThrA), can catalyze direct aldol reactions using glycine as a donor, see: Fesko, K.; Gruber-Khadjawi, M. ChemCatChem 2013, 5, 1248-1272 and references therein
6. Gulevich, A. V.; Zhdanko, A. G.; Orru, R. V. A.; Nenajdenko, V. G. Chem. Rev. 2010, 110, 5235-5331
7. Xue, M.-X.; Guo, C.; Gong, L.-Z. Synlett 2009, 13, 2191-2197
8. Yoshino, T.; Morimoto, H.; Lu, G.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 17082-17083
9. Shirakawa, S.; Ota, K.; Terao, S. J.; Maruoka, K. Org. Biomol. Chem. 2012, 10, 5753-5755
10. Ji, C.-B.; Liu, Y.-L.; Cao, Z.-Y.; Zhang, Y.-Y.; Zhou, J. Tetrahedron Lett. 2011, 52, 6118-6121
11. Gasparski, C. M.; Miller, M. J. Tetrahedron 1991, 47, 5367-5378
12. Mettah, S.; Srikanth, G. S. C.; Dangerfield, B. S.; Castle, S. L. J. Org. Chem. 2004, 69, 6489-6492
13. Ma, B.; Parkinson, J. L.; Castle, S. L. Tetrahedron Lett. 2007, 48, 2083-2086
14. Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 4542-4544
15. Ooi, T.; Kameda, M.; Tani-guchi, M.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 9685-9694
16. Kano, T.; Lan, Q.; Wang, X.; Maruoka, K. Adv. Synth. Catal. 2007, 349, 556-560
17. Kitamura, M.; Shirakawa, S.; Arimura, Y.; Wang, X.; Maruoka, K. Chem.-Asian J. 2008, 3, 1702-1714
18. Yoshikawa, N.; Shibasaki, M. Tetrahedron 2002, 58, 8289-8298
19. Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846
20. Kobayashi, J.; Nakamura, M.; Mori, Y.; Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2004, 126, 9192-9193
21. Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003-12004
22. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497-2500
23. Trost, B. M.; Fettes, A.; Shireman, B. T. J. Am. Chem. Soc. 2004, 126, 2660-2661
24. Trost, B. M.; Shin, S.; Sclafani, J. A. J. Am. Chem. Soc. 2005, 127, 8602-8603
25. Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367-3368
26. Trost, B. M.; Michaelis, D. J.; Truica, M. I. Org. Lett. 2013, 15, 4516-4519
27. Trost, B. M.; Amans, D.; Seganish, W. M.; Chung, C. K. J. Am. Chem. Soc. 2009, 131, 17087-17089
28. 4 is accessible in two steps from (S)-pyroglutamic acid; see: Rudolph, A. C.; Machauer, R.; Martin, S. F. Tetrahedron Lett. 2004, 45, 4895-4898
29. 8 is accessible in four steps from (S)-pyroglutamic acid, see: Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1998, 39, 4789-4792
30. For a 2,5-disubstituted ProPhenol type ligand, see: Kim, Y. B.; Kim, M. K.; Kang, S. H.; Kim, Y. H. Synlett 2005, 1995-1998