Stereochemistry as a tool in deciphering the processes of a tandem iminium cyclization and smiles rearrangement

Journal of Organic Chemistry

Volumn 75, Issue 23, 2010, Pages 8147-8154

  Xiang, Jinbao ^a   Zhu, Tong ^a   Dang, Qun ^a   Bai, Xu ^a  

^a JILIN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOCATIONS; CHIRAL ALDEHYDE; CIS ISOMERS; DIASTEREOMERIC; IMINIUM; L-PROLINOL; METHOXYANILINE; NUCLEOPHILIC SUBSTITUTIONS; REACTION PROCESS; SMILES REARRANGEMENT; STERIC HINDRANCES; TANDEM REACTION; TRANS ISOMERS; TRANSITION STATE;

ALDEHYDES; ISOMERS; STEREOCHEMISTRY;

CYCLIZATION;

1 CHLORO 5 (4 CHLOROPHENYL) 6 (PYRROLIDIN 2 YL) 5,6 DIHYDROPYRROLO[1,2 F]PTERIDINE; 1 CHLORO 5 (4 METHOXYPHENYL) 6 (PYRROLIDIN 2 YL) 5,6 DIHYDROPYRROLO[1,2 F]PTERIDINE; 1 CHLORO 5 (4 METHYLPHENYL) 6 (PYRROLIDIN 2 YL) 5,6 DIHYDROPYRROLO[1,2 F]PTERIDINE; 1 CHLORO 5 PHENYL 6 (PYRROLIDIN 2 YL) 5,6 DIHYDROPYRROLO[1,2 F]PTERIDINE; 4 CHLORO 11,12 DIHYDRO 10H PYRIMIDO[4,5 B]DIPYRROLO[1,2D:1',2' G][1,4]DIAZEPINE; 4 CHLORO 9A,10,11,12 TETRAHYDRO 9H PYRIMIDO[4,5 B]DIPYRROLO[1,2 D:1',2' G][1,4]DIAZEPIN 9 OL; 4 CHLORO N (4 CHLOROPHENYL) 9A,10,11,12 TETRAHYDRO 9H PYRIMIDO[4,5 B]DIPYRROLO[1,2 D:1',2' G][1,4]DIAZEPIN 9 AMINE; 4 CHLORO N (4 METHOXYPHENYL) 9A,10,11,12 TETRAHYDRO 9H PYRIMIDO[4,5 B]DIPYRROLO[1,2 D:1',2' G][1,4]DIAZEPIN 9 AMINE; 4 CHLORO N (4 METHYLPHENYL) 9A,10,11,12 TETRAHYDRO 9H PYRIMIDO[4,5 B]DIPYRROLO[1,2 D:1',2' G][1,4]DIAZEPIN 9 AMINE; 4 CHLORO N (4 NITROPHENYL) 9A,10,11,12 TETRAHYDRO 9H PYRIMIDO[4,5 B]DIPYRROLO[1,2 D:1',2' G][1,4]DIAZEPIN 9 AMINE; 4 CHLORO N PHENYL 9A,10,11,12 TETRAHYDRO 9H PYRIMIDO [4,5 B]DIPYRROLO[1,2 D:1',2' G][1,4]DIAZEPIN 9 AMINE; 5 BENZYL 1 CHLORO N (4 CHLOROPHENYL) 6,7 DIHYDRO 5H PYRIMIDO[4,5 B]PYRROLO[1,2 D][1,4]DIAZEPIN 7 AMINE; ALDEHYDE; DIAZEPINE DERIVATIVE; IMINE; PYRIMIDO[4,5 B]DIPYRROLO[1,2 D 1',2' G][1,4]DIAZEPIN 9 AMINE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; PHASE TRANSITION; REACTION ANALYSIS; SMILES REARRANGEMENT; STEREOCHEMISTRY; STEREOSPECIFICITY; TANDEM IMINIUM CYCLIZATION; TRANS ISOMER;

ANILINE COMPOUNDS; CATALYSIS; CATIONS; CYCLIZATION; IMINES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 78650265613     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101798p     Document Type: Article

References (36)

1. Savéant, J.-M. Chem. Rev. 2008, 108, 2348
2. Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326
3. Sivaguru, J.; Solomon, M. R.; Poon, T.; Jockusch, S.; Bosio, S. G.; Adam, W.; Turro, N. J. Acc. Chem. Res. 2008, 41, 387
4. Abraham, C. J.; Paull, D. H.; Bekele, T.; Scerba, M. T.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 2008, 130, 17085
5. Moriarty, R. M.; Tyagi, S.; Ivanov, D.; Constantinescu, M. J. Am. Chem. Soc. 2008, 130, 7564
6. Simón, L.; Goodman, J. M. J. Am. Chem. Soc. 2009, 131, 4070
7. Viciu, M. S.; Gupta, L.; Collum, D. B. J. Am. Chem. Soc. 2010, 132, 6361
8. Widenhoefer, R. A. Acc. Chem. Res. 2002, 35, 905
9. Padwa, A. J. Org. Chem. 2009, 74, 6421
10. Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311
11. Karadeolian, A.; Kerr, M. A. J. Org. Chem. 2007, 72, 10251
12. Kumpaty, H. J.; Van Linn, M. L.; Kabir, M. S.; Fösterling, F. H.; Deschamps, J. R.; Cook, J. M. J. Org. Chem. 2009, 74, 2771
13. Van Linn, M. L.; Cook, J. M. J. Org. Chem. 2010, 75, 3587
14. Xiang, J.; Zheng, L.; Chen, F.; Dang, Q.; Bai, X. Org. Lett. 2007, 9, 765
15. Xiang, J.; Zheng, L.; Xie, H.; Hu, X.; Dang, Q.; Bai, X. Tetrahedron 2008, 64, 9101
16. Xiang, J.; Xie, H.; Wen, D.; Dang, Q.; Bai, X. J. Org. Chem. 2008, 73, 3281
17. Saito, M.; Kawamura, M.; Hiroya, K.; Ogasawara, K. Chem. Commum. 1997, 765
18. Dinsmore, C. J.; Zartman, C. B.; Baginsky, W. F.; O'Neill, T. J.; Koblan, K. S.; Chen, I.-W.; McLoughlin, D. A.; Olah, T. V.; Huff, J. R. Org. Lett. 2000, 2, 3473
19. Chihab-Eddine, A.; Daïch, A.; Jilale, A.; Decroix, B. Tetrahedron Lett. 2001, 42, 573
20. Mecozzi, T.; Petrini, M.; Profeta, R. Tetrahedron: Asymmetry 2003, 14, 1171
21. Damon, D. B.; Dugger, R. W.; Magnus-Aryitey, G.; Ruggeri, R. B.; Wester, R. T.; Tu, M.; Abramov, Y. Org. Process Res. Dev. 2006, 10, 464
22. Parikh, J. R.; Doering, W. v. E. J. Am. Chem. Soc. 1967, 89, 5505
23. Shiue, J.-S.; Lin, M.-H.; Fang, J.-M. J. Org. Chem. 1997, 62, 4643
24. Kawamoto, T.; Tomimatsu, K.; Ikemoto, T.; Abe, H.; Hamamura, K.; Takatani, M. Tetrahedron Lett. 2000, 41, 3447
25. Almenningen, A.; Bastiansen, O.; Fernholt, L.; Cyvin, B. N.; Cyvin, S. J.; Samdal, S. J. Mol. Struct. 1985, 128, 59
26. Tanabe, Y.; Mizuhata, Y.; Tokitoh, N. Organometallics 2010, 29, 721
27. Han, D.; Fösterling, F. H.; Deschamps, J. R.; Parrish, D.; Liu, X.; Yin, W.; Huang, S.; Cook, J. M. J. Nat. Prod. 2007, 70, 75
28. Reetz, M. T.; Jung, A. J. Am. Chem. Soc. 1983, 105, 4833
29. Reetz, M. T.; Hüellmann, M.; Seitz, T. Angew. Chem., Int. Ed. Engl. 1987, 26, 477
30. Reetz, M. T. Acc. Chem. Res. 1993, 26, 462
31. Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191
32. Cox, E. D.; Hamaker, L. K.; Li, J.; Yu, P.; Czerwinski, K. M.; Deng, L.; Bennett, D. W.; Cook, J. M. J. Org. Chem. 1997, 62, 44
33. Cabanal-Duvillard, I.; Berrien, J.-F.; Ghosez, L.; Husson, H.-P.; Royer, J. Tetrahedron 2000, 56, 3763
34. Cimarelli, C.; Palmieri, G.; Volpini, E. Tetrahedron 2001, 57, 6089
35. Koiwa, M.; Hareau, G. P-J.; Morizono, D.; Sato, F. Tetrahedron Lett. 1999, 40, 4199
36. Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Brillet, C.; García-Granda, S.; Piñera-Nicolás, A.; Vázquez, J. T. J. Am. Chem. Soc. 1999, 121, 4516