Catalyst-directed diastereoselectivity in hydrogenative couplings of acetylene to α-chiral aldehydes: Formal synthesis of all eight L-hexoses

Organic Letters

Volumn 10, Issue 18, 2008, Pages 4133-4135

  Man, Soo Bong ^a   Kong, Jong Rock ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ALDEHYDE; HEXOSE; HYDROGEN;

ARTICLE; CATALYSIS; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM; SYNTHESIS;

ACETYLENE; ALDEHYDES; CATALYSIS; HEXOSES; HYDROGEN; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 55949087716     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8018874     Document Type: Article

References (33)

1. For selected reviews encompassing de novo synthetic approaches to monosaccharides, see: (a) Zamoiski, A.; Banaszek, A.; Grynkiewicz, G. Adv. Carbohydr. Chem. Biochem. 1982, 40, 1.
2. (b) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195.
3. (c) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443.
4. (d) Vogel, P. In Glycoscience; Fraser-Reid, B. O., Tatsuta, K., Thiem, J., Eds.; Springer-Verlag: Berlin, 2001; Vol. II, Chapter 4.4, p 1023.
5. (a) Fischer, E. Ber. Dtsch. Chem. Ges. 1890, 23, 370.
6. (b) Fischer, E. Ber. Dtsch. Chem. Ges. 1890, 23, 799.
7. For monosaccharide synthesis employing alkene enantioselective epoxidation, see: Ko, S. Y.; Lee, A. W. M.; Masamune, S.; Reed, L. A., III; Sharpless, K. B.; Walker, F. J. Science 1983, 949. Also see ref 9a.
8. For monosaccharide synthesis employing enantioselective alkene dihydroxylation, see: (a) Harris, J. M.; Keranen, M. D.; O'Doherty, G. A. J. Org. Chem. 1999, 64, 2982.
9. (b) Takeuchi, M.; Taniguchi, T.; Ogasawara, K. Synthesis 1999, 341.
10. (c) Harris, J. M.; Keranen, M. D.; Nguyen, H.; Young, V. G.; O'Doherty, G. A. Carbohydr. Res. 2000, 328, 17.
11. (d) Ahmed, Md. M.; Berry, B. P.; Hunter, T. J.; Tomcik, D. J.; O'Doherty, G. A. Org. Lett. 2005, 7, 745.
12. (e) Ermolenka, L.; Sasaki, N. A. J. Org. Chem. 2006, 71, 693.
13. For monosaccharide synthesis employing enantioselective Payne rearrangement, see: Covell, D. J.; Vermeulen, N. A.; Labenz, N. A.; White, M. C. Angew. Chem., Int. Ed. 2006, 45, 8217.
14. For monosaccharide synthesis employing enantioselective organocatalyzed aldol addition, see: (a) Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752.
15. (b) Enders, D.; Grondal, C. Angew. Chem., Int. Ed. 2005, 44, 1210.
16. For hydrogen-mediated couplings of acetylene to carbonyl compounds and imines, see: (a) Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 16040.
17. (b) Skucas, E.; Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 7242.
18. For selected reviews of hydrogenative C-C coupling, see: (a) Ngai, M.-Y.; Kong, J.-R.; Krische, M. J. J. Org. Chem. 2007, 72, 1063.
19. (b) Iida, H.; Krische, M. J. Top. Curr. Chem. 2007, 279, 77.
20. (c) Skucas, E.; Ngai, M.-Y.; Komanduri, V.; Krische, M. J. Acc. Chem. Res. 2007, 40, 1394.
21. For selected examples of catalyst directed diastereofacial selection, see: (a) Minami, N.; Ko, S. S.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 1109.
22. (b) Kobayashi, S.; Ohtsubo, A.; Mukaiyama, T. Chem. Lett. 1991, 831.
23. (c) Hammadi, A.; Nuzillard, J. M.; Poulin, J. C; Kagan, H. B. Tetrahedron: Asymmetry 1992, 3, 1247.
24. (d) Doyle, M. P.; Kalinin, A. V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837.
25. (e) Trost, B. M.; Calkins, T. L.; Oertelt, C.; Zambrano, J. Tetrahedron Lett. 1998, 39, 1713.
26. (f) Balskus, E.; E. P.; Jacobsen, E. N. Science 2007, 317, 1736. Also, see ref 3.
27. For exhaustive hydrogenation of conjugated dienes catalyzed by iridium, see: Cui, X.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 14212, and references therein.
28. O-Benzyl derivative of adduct 1b: (a) Ito, M; Kibayashi, C. Tetrahedron 1991, 45, 9329.
29. Adduct 2c: (b) Fujita, M.; Hiyama, T. J. Org. Chem. 1988, 55, 5415.
30. Adduct 3b: (c) Reetz, M. T.; Rolfing, K.; Greibenow, N. Tetrahedron Lett. 1994, 35, 1969.
31. Adduct 4b: (d) Barrow, J. C.; Coburn, C. A.; Nantermet, P. G.; Selnick, H. G.; Stachel, S. J.; Stanton, M. G.; Stauffer, S. R.; Zhuang, L.; Davis, J. R. International Patent WO 2005/ 065195, 2005.
32. For Johnson-Lemieux reaction of conjugated dienes, see: (a) Sakya, S. M.; Suarez-Contreras, M.; Dirlam, J. P.; O'Connell, T. N.; Hayashi, S. F.; Santoro, S. L.; Kamicker, B. J.; George, D. M.; Ziegler, C. B. Bioorg. Med. Chem. Lett. 2001, 11, 2751.
33. (b) Cho, C.-W.; Krische. M. J. Org. Lett. 2006, 8, 891.