Modular and stereoselective synthesis of tetrasubstituted helical alkenes via a palladium-catalyzed domino reaction

Organic Letters

Volumn 14, Issue 14, 2012, Pages 3648-3651

  Liu, Hongqiang ^a   El Salfiti, Mohamed ^a   Chai, David I ^a   Auffret, Jérémy ^a   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; ALKENE; NORBORNANE DERIVATIVE; NORBORNENE ANHYDRIDE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; ANHYDRIDES; CATALYSIS; MOLECULAR STRUCTURE; NORBORNANES; PALLADIUM; STEREOISOMERISM;

EID: 84864123932     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301495q     Document Type: Article

References (26)

1. Balzani, V., Credi, A., Venturi, M. Molecular Devices and Machines-Concepts and Perspectives for the Nanoworld, 2 nd ed.; Wiley- VCH: Weinheim, 2008.
2. Sauvage, J.-P., Ed. Molecular Machines and Motors; Springer: New York, 2001.
3. Feringa, B. L. J. Org. Chem. 2007, 72, 6635-6652 and references therein
4. Feringa, B. L.; van Delden, R. A.; Koumura, N.; Geertsema, E. M. Chem. Rev. 2000, 100, 1789-1816 and references therein
5. Ruangsupapichat, N.; Pollard, M. M.; Harutyunyan, S. R.; Feringa, B. L. Nat. Chem. 2011, 3, 53-60
6. Tietze, L. F.; Düfert, M. A.; Lotz, F.; Sçlter, L.; Oum, K.; Lenzer, T.; Beck, T.; Herbst-Irmer, R. J. Am. Chem. Soc. 2009, 131, 17879-17884
7. Wang, J.; Feringa, B. L. Science 2011, 331, 1429-1432
8. Tietze, L. F.; Düfert, M. A.; Hungerland, T.; Oum, K.; Lenzer, T. Chem.-Eur. J. 2011, 17, 8452-8461
9. Tietze, L. F.; Hungerland, T.; Dufert, A.; Objartel, I.; Stalke, D. Chem.-Eur. J. 2012, 18, 3286-3291
10. Hojo, D.; Noguchi, K.; Tanaka, K. Angew. Chem., Int. Ed. 2009, 48, 8129-8132
11. Pijper, T. C; Pijper, D.; Pollard, M. M.; Dumur, F.; Davey, S. G.; Meetsma, A.; Feringa, B. L. J. Org. Chem. 2010, 75, 825-838
12. Gericke, K. M.; Chai, D. I.; Bieler, N.; Lautens, M. Angew. Chem. 2009, 121, 1475-1479
13. Angew. Chem., Int. Ed. 2009, 48, 1447-1451.
14. Catellani, M.; Frignani, F.; Rangoni, A. Angew. Chem., Int. Ed. 1997, 36, 119-122
15. Topics in Current Chemistry: C-H Activation; Yu, J.-Q.; Shi, Z., Eds.; Springer: Berlin, 2010; Vol. 292, pp 1-33.
16. Myers, A. G.; Goldberg, S. D. Angew. Chem., Int. Ed. 2000, 29, 2732
17. Smith, A. B.; Fox, R. J.; Vanecko, J. A. Org. Lett. 2005, 7, 3099
18. The side product formation was also observed by others. See: Fürstner, A.; Wuchrer, M. Chem.-Eur. J. 2006, 12, 76-89
19. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467-4470
20. Appel, R. Angew. Chem., Int. Ed. Engl. 1975, 14, 801-811
21. Gericke, K. M.; Chai, D. I.; Lautens, M. Tetrahedron 2008, 64, 6002-6014
22. A chelation model between the palladium and hydroxyl substituent during carbopalladation onto the alkyne was proposed to explain the complete diastereoselectivity in the tetrasubstituted alkene formation via a domino reaction. See ref 3 and Machotta, A. B.; Straub, B. F.; Oestreich, M. J. Am. Chem. Soc. 2007, 129, 13455-13463
23. Johnson, F. Chem. Rev. 1968, 68, 375-411
24. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860
25. van Delden, R. A.; ter Wiel, M. K. J.; Pollard, M. M.; Vicario, J.; Koumura, N.; Feringa, B. L. Nature 2005, 437, 1337
26. Eelkema, R.; Pollard, M. M.; Vicario, J.; Katsonis, N.; Ramon, B. S.; Bastiaansen, C. W. M.; Broer, D. J.; Feringa, B. L. Nature 2006, 440, 163