Catalytic enantioselective synthesis of chiral isatin derivatives by an aldol approach

Synlett

Volumn 23, Issue 12, 2012, Pages 1783-1788

  Yanagisawa, Akira ^a   Kushihara, Naoyuki ^a   Sugita, Takuya ^a   Yoshida, Kazuhiro ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

aldol reaction; alkenyl ester; asymmetric catalysis; isatin; tin

Indexed keywords

1 BENZYL 3 HYDROXY 3 (6 METHOXY 1 OXO 1,2,3,4 TETRAHYDRONAPHTHALEN 2 YL)INDOLIN 2 ONE; 2,2' DIHYDROXY 1,1' BINAPHTHYL; 3 HYDROXY 2 OXINDOLE; 4 CHROMANONE DERIVATIVE; 6 METHOXY 1 TETRALONE ALKENYL TRICHLOROACETIC ACID; ALKENYL GROUP; ALKENYL TRICHLOROACETIC ACID; ALKENYL TRIFLUOROACETIC ACID; ISATIN; ISATIN DERIVATIVE; METHANOL; N BENZYL ISATIN; N TOSYL ISATIN; NITROGEN; OXINDOLE; TIN DIBROMIDE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; QUANTITATIVE ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84863109231     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1316551     Document Type: Article

References (25)

1. Tokunaga T, Hume WE, Umezome T, Okazaki K, Ueki Y, Kumagai K, Hourai S, Nagamine J, Seki H, Taiji M, Noguchi H, Nagata R. J. Med. Chem.: 2001; 44 4641
2. Kitajima M, Mori I, Arai K, Kogure N, Takayama H. Tetrahedron Lett.: 2006; 47 3199
3. Kamano Y, Zhang H.-P, Ichihara Y, Kizu H, Komiyama K, Pettit GR. Tetrahedron Lett.: 1995; 36 2783
4. Zhang H.-P, Kamano Y, Ichihara Y, Kizu H, Komiyama K, Itokawa H, Pettit GR. Tetrahedron: 1995; 51 5523
5. Takayama H, Shimizu T, Sada H, Harada Y, Kitajima M, Aimi N. Tetrahedron: 1999; 55 6841
6. Kamano Y, Kotake A, Hashima H, Hayakawa I, Hiraide H, Zhang H.-P, Kizu H, Komiyama K, Hayashi M, Pettit GR. Collect. Czech. Chem. Commun.: 1999; 64 1147
7. Luppi G, Cozzi PG, Monari M, Kaptein B, Broxterman QB, Tomasini C. J. Org. Chem.: 2005; 70 7418
8. Chen G, Wang Y, He H, Gao S, Yang X, Hao X. Heterocycles: 2006; 68 2327
9. Luppi G, Monari M, Corrêa RJ, Violante FA, Pinto AC, Kaptein B, Broxterman QB, Garden SJ, Tomasini C. Tetrahedron: 2006; 62 12017
10. Malkov AV, Kabeshov MA, Bella M, Kysilka O, Malyshev DA, Pluháčková K, Kočovsk P. Org. Lett.: 2007; 9 5473
11. Chen J.-R, Liu X.-P, Zhu X.-Y, Li L, Qiao Y.-F, Zhang J.-M, Xiao W.-J. Tetrahedron: 2007; 63 10437
12. Corrêa RJ, Garden SJ, Angelici G, Tomasini C. Eur. J. Org. Chem.: 2008; 736
13. Nakamura S, Hara N, Nakashima H, Kubo K, Shibata N, Toru T. Chem.-Eur. J.: 2008; 14 8079
14. Hara N, Nakamura S, Shibata N, Toru T. Chem.-Eur. J.: 2009; 15 6790
15. Itoh T, Ishikawa H, Hayashi Y. Org. Lett.: 2009; 11 3854
16. Chen W.-B, Du X.-L, Cun L.-F, Zhang X.-M, Yuan W.-C. Tetrahedron: 2010; 66 1441
17. Raj M, Veerasamy N, Singh VK. Tetrahedron Lett.: 2010; 51 2157
18. Hara N, Nakamura S, Shibata N, Toru T. Adv. Synth. Catal.: 2010; 352 1621
19. Hara N, Nakamura S, Funahashi Y, Shibata N. Adv. Synth. Catal.: 2011; 353 2976
20. Kinsella M, Duggan PG, Lennon CM. Tetrahedron: Asymmetry: 2011; 22 1423
21. Liu Y.-L, Zhou J. Chem. Commun.: 2012; 48 1919
22. Hanhan NV, Sahin AH, Chang TW, Fettinger JC, Franz AK. Angew. Chem. Int. Ed.: 2010; 49 744
23. Aikawa K, Mimura S, Numata Y, Mikami K. Eur. J. Org. Chem.: 2011; 62
24. Gil J, Medio-Simon M, Mancha G, Asensio G. Eur. J. Org. Chem.: 2005; 1561
25. Claraz A, Leroy J, Oudeyer S, Levacher V. J. Org. Chem.: 2011; 76 6457