Asymmetric synthesis of trans-2,3-disubstituted indoline derivatives

Journal of Organic Chemistry

Volumn 77, Issue 1, 2012, Pages 808-812

  Kang, Kyoung Hee ^a   Do, Junghwan ^a   Park, Yong Sun ^a  

^a Konkuk University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; ELECTROPHILIC SUBSTITUTIONS; INDOLINE DERIVATIVES; NUCLEOPHILIC SUBSTITUTIONS; SIMPLE PROTOCOL; TWO-STEP PROCESS; UNSATURATED ALDEHYDES;

CHEMISTRY; ORGANIC COMPOUNDS;

ALDEHYDES;

2 BENZYL N PIVALOYLANILINE; ALDEHYDE DERIVATIVE; ANILINE DERIVATIVE; INDOLE DERIVATIVE; SPARTEINE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; ELECTROPHILICITY; ENANTIOSELECTIVITY; NUCLEOPHILICITY; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

ALDEHYDES; CATALYSIS; INDOLES; SPARTEINE; STEREOISOMERISM;

EID: 84862907639     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2023526     Document Type: Article

References (18)

1. Schammel, A. W.; Boal, B. W.; Zu, L.; Mesganaw, T.; Garg, N. K. Tetrahedron 2010, 66, 4687
2. Liu, D.; Zhao, G.; Xiang, L. Eur. J. Org. Chem. 2010, 3975
3. García Ruano, J. L.; Alemán, J.; Catalán, S.; Marcos, V.; Monteagudo, S.; Parra, A.; del Pozo, C.; Fustero, S. Angew. Chem., Int. Ed. 2008, 47, 7941
4. García Ruano, J. L.; Parra, A.; Marcos, V.; del Pozo, C.; Catalán, S.; Monteagudo, S.; Fustero, S.; Poveda, A. J. Am. Chem. Soc. 2009, 131, 9432
5. Han, B.; Xiao, Y.-C.; Yao, Y.; Chen, Y.-C. Angew. Chem., Int. Ed. 2010, 49, 10189
6. Wang, D.-S.; Chen, Q.-A.; Yu, C.-B.; Zhou, Y.-G.; Zhang, X. J. Am. Chem. Soc. 2010, 132, 8909
7. Park, Y. S.; Yum, E. K.; Basu, A.; Beak, P. Org. Lett. 2006, 8, 2667
8. Kim, Y.; Shin, E.-K.; Beak, P.; Park, Y. S. Synthesis 2006, 3805
9. Berts, W.; Luthman, K. Tetrahedron 1999, 55, 13819
10. Callaghan, O.; Lampard, C.; Kennedy, A. R.; Murphy, J. A. Tetrahedron Lett. 1999, 40, 161
11. Noguchi, T.; Tanaka, N.; Nishimata, T.; Goto, R.; Hayakawa, M.; Sugidachi, A.; Ogawa, T.; Asai, F.; Fujimoto, K. Chem. Pharm. Bull. 2007, 55, 1494
12. Cherney, R. J.; Wang, L. J. Org. Chem. 1996, 61, 2544
13. Aoyagu, Y.; Gui, M.-Y.; Jin, Y.-R.; Li, X.-W.; Noguchi, T.; Fukaya, H.; Hasuda, T.; Takeya, K. Tetrahedron Lett. 2004, 45, 1421
14. Métro, T.-X.; Fayet, C.; Arnaud, F.; Rameix, N.; Fraisse, P.; Janody, S.; Sevrin, M.; George, P.; Vogel, R. Synlett 2011, 684
15. Parcerisa, J.; Romero, M.; Pujol, M. D. Tetrahedron 2008, 64, 500
16. Wang, Z.; Wan, W.; Jiang, H.; Hao, J. J. Org. Chem. 2007, 72, 9364
17. 1H NMR of authentic material in the following literature. McComas, C. C.; Gilbert, E. J.; Vranken, D. L. V. J. Org. Chem. 1997, 62, 8600
18. Wardrop, A. W. H.; Sainsbury, G. L.; Harrison, J. M.; Inch, T. D. J. Chem. Soc., Perkin Trans. 1 1976, 1279