Lewis acid catalyzed cyclization of glycals/2-deoxy-d-ribose with arylamines: Additional findings on product structure and reaction diastereoselectivity

Journal of Organic Chemistry

Volumn 76, Issue 21, 2011, Pages 8833-8839

  Du, Chengtang ^a,b   Li, Fulong ^a,c   Zhang, Xuefeng ^a   Hu, Wenxiang ^b   Yao, Qizheng ^c   Zhang, Ao ^b  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b CAPITAL NORMAL UNIVERSITY   (China)

^c CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL AMINES; CYCLIZATION REACTIONS; DIASTEREO-SELECTIVITY; DIASTEREOMERIC; DIASTEREOMERIC RATIOS; DIASTEREOMERS; GLYCALS; LEWIS ACID; MONTMORILLONITE KSF; PRODUCT STRUCTURE;

CATALYSIS; CLAY MINERALS; STEREOSELECTIVITY;

CYCLIZATION;

2 DEOXYRIBOSE; AROMATIC AMINE; ELECTROPHILE; GLYCAL; LEWIS ACID; MONTMORILLONITE; QUINOLINE DERIVATIVE; TETRAHYDROFURAN; TETRAHYDROQUINOLINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; STEREOCHEMISTRY;

AMINES; BENTONITE; CATALYSIS; CYCLIZATION; FURANS; LEWIS ACIDS; MOLECULAR STRUCTURE; QUINOLINES; RIBOSE; STEREOISOMERISM;

EID: 80055087230     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2015483     Document Type: Article

References (22)

1. Postema, M. H. D. Tetrahedron 1992, 48, 8545
2. Ferrier, R. J.; Prasad, N. J. Chem. Commun. 1969, 20, 570
3. Ferrier, R. J.; Zubkov, O. A. Org. React. 2003, 62, 569
4. Ferrier, R. J. Top. Curr. Chem. 2001, 215, 153
5. Brawn, R. A.; Panek, J. S. Org. Lett. 2010, 12, 4624
6. Yeager, A. R.; Min, G. K.; Porco, J. A., Jr. ; Schaus, S. E. Org. Lett. 2006, 8, 5065
7. Clark, J. H. Acc. Chem. Res. 2002, 35, 791
8. Minzuno, N.; Misono, M. Chem. Rev. 1998, 98, 199
9. Yadav, J. S.; Reddy, B. V. S.; Rao, K. V.; Raj, K. S.; Prasad, A. R.; Kumar, S. K.; Kunwar, A. C.; Jayaprakash, P.; Jagannath, B. Angew. Chem., Int. Ed. 2003, 42, 5198
10. Li, Z.; Zhang, J.; Li, C. Tetrahedron Lett. 2003, 44, 153
11. Yadav, J. S.; Reddy, B. V. S.; Srinivas, M.; Padmavani, B. Tetrahedron 2004, 60, 3261
12. Yadav, J. S.; Reddy, B. V. S.; Parimala, G.; Raju, A. K. Tetrahedron Lett. 2004, 45, 1543
13. Yadav, J. S.; Reddy, B. V. S.; Srinivas, M.; Vishnumurthy, P.; Narsimulu, K.; Kunwar, A. C. Synthesis 2006, 17, 2923
14. Rafiee, E.; Azad, A. Bioorg. Med. Chem. Lett. 2007, 17, 2756
15. Ding, C.; Tu, S.; Li, F.; Wang, Y.; Yao, Q.; Hu, W.; Xie, H.; Meng, L.; Zhang, A. J. Org. Chem. 2009, 74, 6111
16. Maugel, N.; Snider, B. Org. Lett. 2009, 11, 4926
17. Ding, C.; Tu, S.; Yao, Q.; Li, F.; Wang, Y.; Hu, W.; Zhang, A. Adv. Synth. Catal. 2010, 352, 847
18. Li, F.; Ding, C.; Wang, M.; Yao, Q.; Zhang, A. J. Org. Chem. 2011, 76, 2820
19. Shull, B. K.; Wu, Z.; Koreeda, M. J. Carbohydr. Chem. 1996, 15, 955
20. Leibeling, M.; Koester, D. C.; Pawliczek, M.; Kratzert, D.; Dittrich, B.; Werz, D. B. Bioorg. Med. Chem. 2010, 18, 3656
21. Brawn, R. A.; Panek, J. S. Org. Lett. 2010, 12, 4624
22. Org. Lett. 2010, 12, 5600. The authors originally reported their success in preparation of furanose 13, but later they revised the structure as pyranose 1d