Asymmetric synthesis of cyclic indole aminals via 1,3-stereoinduction

Journal of Organic Chemistry

Volumn 79, Issue 18, 2014, Pages 8533-8540

  Li, Hongmei ^a   Chen, Cheng Yi ^a   Nguyen, Hoa ^a   Cohen, Ryan ^a   Maligres, Peter E ^a   Yasuda, Nobuyoshi ^a   Mangion, Ian ^a   Zavialov, Ilia ^a   Reibarkh, Mikhail ^a   Chung, John Y L ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUPS;

ASYMMETRIC SYNTHESIS; DYNAMIC CRYSTALLIZATION; GENERAL METHODOLOGIES; HIGH YIELD; POTASSIUM PERMANGANATE;

POLYCYCLIC AROMATIC HYDROCARBONS;

ALDEHYDE; INDOLE AMINAL; INDOLE DERIVATIVE; INDOLINE AMINAL; PERMANGANATE POTASSIUM; UNCLASSIFIED DRUG; INDOLE; INDOLINE;

ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CRYSTALLIZATION; DEHYDROGENATION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; INDOLES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84911863400     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501581e     Document Type: Article

References (24)

1. Heys, L.; Moore, C. G.; Murphy, P. J. Chem. Soc. Rev. 2000, 29, 57.
2. Coric, I.; Vellalath, S.; Muller, S.; Cheng, X.; List, B. Top. Organomet. Chem. 2013, 44, 165.
3. Richter, A.; Kocienski, P.; Raubo, P.; Davies, D. E. Anti-Cancer Drug Des. 1997, 12, 217.
4. Coburn, C. A.; Meinke, P. T.; Chang, W.; Fandozzi, C. M.; Graham, D. J.; Hu, B.; Huang, Q.; Kargman, S.; Kozlowski, J.; Liu, R.; McCauley, J. A.; Nomeir, A. A.; Soll, R. M.; Vacca, J. P.; Wang, D.; Wu, H.; Zhong, B.; Olsen, D. B.; Ludmerer, S. W. ChemMedChem 2013, 8, 1930.
5. Kim, H.; Rhee, Y. H. Synlett 2012, 23, 2875 and references cited therein.
6. For a review on N, O-acetals: Warriner, S. Category 4: Compounds with Two Carbon-Heteroatom Bonds. In Science of Synthesis; Bellus, D., Ed.; Thieme: Stuttgart, 2007; Vol. 30, p 7.
7. Chauhan, P.; Chimni, S. S. Tetrahedron: Asymmetry 2013, 24, 343.
8. Li, G.; Fronczek, F. R.; Antilla, J. C. J. Am. Chem. Soc. 2008, 130, 12216.
9. Vellalath, S.; Coric, I.; List, B. Angew. Chem., Int. Ed. 2010, 49, 9749.
10. Other selected examples using chiral phosphric acid cataysts for aminal synthesis: (a) Li, T.-Z; Wang, X.-B; Sha, F.; Wu, X Tetrahedron 2013, 69, 7314.
11. (b) Hashimoto, T.; Nakatsu, H.; Takiguchi, Y.; Maruoka, K. J. Am. Chem. Soc. 2013, 135, 16010.
12. (c) Honjo, T.; Phipps, R. J.; Rauniyar, V.; Toste, F. D. Angew. Chem., Int. Ed. 2012, 51, 9684.
13. Kim, H.; Rhee, Y. H. J. Am. Chem. Soc. 2012, 134, 4011.
14. Li, M.; Luo, B.; Liu, Q.; Hu, Y.; Ganesan, A.; Huang, P.; Wen, S. Org. Lett. 2014, 16, 10.
15. Mangion, I.; Chen, C.-Y; Li, H.; Maligres, P.; Chen, Y.; Christensen, M.; Cohen, R.; Jeon, I.; Klapars, A.; Krska, S.; Nguyen, H.; Reamer, R. A.; Sherry, B. D.; Zavialov, I. Org. Lett. 2014, 2310.
16. Rowland, G. B.; Rowland, E. B.; Liang, Y.; Perman, J. A.; Antilla, J. C. Org. Lett. 2007, 9, 2609.
17. Maruoka, K. Org. Process Res. Dev. 2008, 12, 679-697.
18. Kunz, R. K.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3240.
19. Corminboeuf, O.; Quaranta, L.; Renaud, P.; Liu, M.; Jasperse, C. P.; Sibi, M. P. Chem.. Eur. J. 2003, 9, 28.
20. Chiral indoline synthesis: (a) Wang, D.-S.; Chen, Q.-A.; Li, W.; Yu, C.-G.; Zhou, Y.-G.; Zhang, X. J. Am. Chem. Soc. 2010, 132, 8909.
21. (b) Duan, Y.; Li, L.; Chen, M.-W.; Yu, C.-B.; Fan, H.-J.; Zhou, Y.-G. J. Am. Chem. Soc. 2014, 7688.
22. Brands, K. M. J.; Davies, A. J. Chem. Rev. 2006, 106, 2711.
23. Hara, T.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Tetrahedron Lett. 2003, 44, 6207.
24. Crabtree, R. H. J. Chem. Soc., Dalton Trans. 2001, 2437.