Oxidant-controlled heck-type C-glycosylation of glycals with arylboronic acids: Stereoselective synthesis of aryl 2-deoxy-C-glycosides

Organic Letters

Volumn 11, Issue 8, 2009, Pages 1709-1712

  Xiong, De Cai ^a   Zhang, Li He ^a   Ye, Xin Shan ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE DERIVATIVE; BORONIC ACID DERIVATIVE; DICHLORODICYANOBENZOQUINONE; ETHER DERIVATIVE; GLYCOSIDE; OXIDIZING AGENT;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; GLYCOSYLATION; STEREOISOMERISM; SYNTHESIS;

BENZOQUINONES; BORONIC ACIDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; ETHERS, CYCLIC; GLYCOSIDES; GLYCOSYLATION; MOLECULAR STRUCTURE; OXIDANTS; STEREOISOMERISM;

EID: 65249173020     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900273d     Document Type: Article

References (23)

1. Bililign, T.; Griffith, B. R.; Thorson, J. S. Nat. Prod. Rep. 2005, 22, 742-760, and references therein.
2. (a) Qin, H.-L.; Lowe, J. T.; Panek, J. S. J. Am. Chem. Soc. 2007, 129, 38-39.
3. (b) Reddv, C. R.; Reddv. G. B.; Rao, C. L. Tetrahedron Lett. 2008, 49, 863-866.
4. (a) Steihuebel, D. P.; Fleming, J. F.; DuBios, J. Org. Lett. 2002, 4, 293-295.
5. (b) Price, S.; Edwards, S.; Wu, T.; Minehan, T. Tetrahedron Lett. 2004, 45, 5197-5201, and references therein.
6. (c) Ramnauth, J.; Poulin, O.; Rakhit, S.; Maddaford. S. P. Qrg. Lett. 2001, 3, 2013-2015.
7. (a) Benhaddou, R.; Czernecki. S.; Ville. G. J. Org. Chem. 1992, 57, 4612-1616.
8. (b) Ramnauth, J.; Poulin, O.; Bratovanov. S. S.; Rakhit. S.; Maddaford, S. P. Org. Lett. 2001, 3, 2571-2573.
9. (a) Czernecki. S.; Dechavanne. V. Can. J. Chem. 1983, 61, 533- 540.
10. (b) Cheng, J. C.-Y.; Daves, G. D.; Jr. J.Org. Chem. 1987, 52, 3083- 3090.
11. (c) Daves, G. D., Jr. Acc. Chem. Res. 1990, 23, 201-206.
12. Arai. I.: Daves, G. D.; Jr. J.Am. Chem. Soc. 1981, 103, 7683.
13. Miyaura, N.; Suzuki. A. Chem. Rev. 1995, 95, 2457-2483.
14. Kotha, S.: Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633- 9695.
15. de la Figuera. N.; Forns. P.; Fernàndez, J.-C; Fiol. S.; Fernández- Fomer. D.; Albericio, F. Tetrahedron Lett. 2005, 46, 7271-7274.
16. Yin, G.; Liu, G. Angew. Chem., Int. Ed. 2008, 47, 5442-5445, and references therein.
17. Lu, X. Top. Catal. 2005, 35, 73-86.
18. Brakta, M.; Farr, R. N.; Chaguir, B.; Massiot, G.; Lavaud, C; Anderson. W. R., Jr.; Sinou, D.; Daves, G. D.; Jr. J. Org. Chem. 1993, 58, 2992-2998.
19. (a)Tanemura, K.; Suzuki, T.; Horaguchi, T. J. Chem. Soc, Perkin Trans. 1 1992, 2997-2998.
20. (b) Tanemura. K.; Suzuki, T.; Horaguchi, T. Bull. Chem. Soc Jpn. 1994, 67, 290-292.
21. (a) lto, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011- 1013.
22. (b) Porth, S.; Bats, J. W.; Trauner. D.; Giester. G.; Mulzer, J. Angew. Chem., Int. Ed. 1999, 38, 2015-2016.
23. Evans. P. A; Longmire, J. M; Modi, D. P. Tetrahedron Lett. 1995, 36, 3985-3988.