Low-temperature Heck reactions of axially chiral o-iodoacrylanilides occur with chirality transfer: Implications for catalytic asymmetric Heck reactions

Journal of the American Chemical Society

Volumn 129, Issue 3, 2007, Pages 494-495

  Lapierre, Andre J B ^a   Geib, Steven J ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILIDE; IODINE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL BOND; CHIRALITY; COMPLEX FORMATION; CYCLIZATION; ENANTIOMER; HECK REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LOW TEMPERATURE; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

ACRYLATES; ALKALOIDS; ANILIDES; CATALYSIS; COLD; CYCLIZATION; HETEROCYCLIC COMPOUNDS; MODELS, CHEMICAL; PALLADIUM; STEREOISOMERISM;

EID: 33846461329     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja067790i     Document Type: Article

References (23)

1. (a) Tietze, L. F.; Ila, H.; Bell, H. P. Chem. Rev. 2004, 104, 3453-3516.
2. (b) Shibasaki, M.; Vogl, E. M.; Ohshima, T. Adv. Synth. Catal. 2004, 340, 1533-1552.
3. (c) Guiry, P. J.; Kiely, D. Curr. Org. Chem. 2004, 8, 781-794.
4. (d) Shibasaki, M.; Miyazaki, F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., de Meijere, A., Eds.; Wiley; New York, 2002; Vol. 1, p 1283-1315.
5. (e) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945-2963.
6. (f) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371-7395.
7. (a) Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477-6487.
8. (b) Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488-6499.
9. (c) Cyclizations under "cationic conditions" with silver additives often provide very different results.
10. (a) Horne, S.; Taylor, N.; Collins, S.; Rodrigo, R. J. Chem. Soc., Perkin Trans. 1 1991, 3047-3051.
11. Curran, D. P.; Hale, G. R.; Geib, S. J.; Balog, A.; Cass, Q. B.; Degani, A. L. G.; Hernandes, M. Z.; Freitas, L. C. G. Tetrahedron: Asymmetry 1997, 8, 3955-3975.
12. (b) Curran, D. P.; Geib, S.; DeMello, N. Tetrahedron 1999, 55, 5681-5704.
13. (c) Curran, D. P.; Liu, W. D.; Chen, C. H.-T. J. Am. Chem. Soc. 1999, 121, 11012-11013.
14. (d) Curran, D. P.; Chen, C. H. T.; Geib, S. J.; Lapierre, A. J. B. Tetrahedron 2004, 60, 4413-4424.
15. (e) Petit, M.; Geib, S. J.; Curran, D. P. Tetrahedron 2004, 60, 7543-7552.
16. (f) Adler, T.; Bonjoch, J.; Clayden, J.; Font-Bardia, M.; Pickworth, M.; Solans, X.; Sole, D.; Vallverdu, L. Org. Biomol. Chem. 2005, 3, 3173-3183.
17. (g) Petit, M.; Lapierre, A. J. B.; Curran, D. P. J. Am. Chem. Soc. 2005, 127, 14994-14995.
18. McDermott, M. C.; Stephenson, G. R.; Hughes, D. L.; Walkington, A. J. Org. Lett. 2006, 8, 2917-2920.
19. Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677-2678.
20. Curran, D. P.; Heffner, T. A. J. Org. Chem. 1990, 55, 4585-4595.
21. The figures illustrate the insertion occurring before formation of the π-complex; however, it is also possible that the π-complex reversibly forms first, or that the two steps occur together.
22. Evidence suggests that related (albeit cationic) insertion reactions are fast relative to N-Ar rotation of anilides bearing bulky o-substituents (ref 3b). See (a) Brown, J. M.; Pérez-Torrente, J. J.; Alcock, N. W.; Clase, H. J. Organometallics 1995, 14, 207-213.
23. (b) Brown, J. M.; Hii, K. K. Angew. Chem., Int. Ed. 1996, 35, 657-659. Alternatively, if N-Ar rotation of 10 is faster than insertion, then axial chirality dictates product configuration in a dynamic thermodynamic resolution.