Palladium(II)-catalyzed enantioselective synthesis of 2-vinyl oxygen heterocycles

Journal of Organic Chemistry

Volumn 77, Issue 4, 2012, Pages 1961-1973

  Cannon, Jeffrey S ^a   Olson, Angela C ^a   Overman, Larry E ^a   Solomon, Nicole S ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b GILEAD SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETATE PRECURSORS; COMPUTATIONAL EXPERIMENT; CYCLIZATION REACTIONS; ENANTIOMERIC PURITY; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; GOOD YIELD; HIGH YIELD; LEAVING GROUPS; OXYGEN HETEROCYCLES;

CATALYSIS; DEUTERIUM; ENANTIOMERS; ENANTIOSELECTIVITY; PALLADIUM COMPOUNDS; PHENOLS; SUBSTITUTION REACTIONS; VOLATILE FATTY ACIDS;

CYCLIZATION;

ACETAMIDE DERIVATIVE; ACETIC ACID DERIVATIVE; ALLYL COMPOUND; BENZOXAZINE DERIVATIVE; CHLORINE DERIVATIVE; DEUTERIUM; OXYGEN DERIVATIVE; PALLADIUM; PHENOL DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; ISOTOPE LABELING; QUANTUM YIELD; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

BENZOXAZINES; CATALYSIS; CHROMANS; COMPUTER SIMULATION; CYCLIZATION; DEUTERIUM; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXYGEN; PALLADIUM; PIPERIDINES; STAINING AND LABELING; STEREOISOMERISM; TRICHLOROACETIC ACID; VINYL COMPOUNDS;

EID: 84857207940     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202553a     Document Type: Article

References (48)

1. Carreño, M. C.; Hernándes-Torres, G.; Urbano, A.; Colobert, F. Eur. J. Org. Chem. 2008, 12, 2035-2038
2. Liu, Y.-C.; Sperry, J.; Rathwell, D. C. K.; Brimble, M. A. Synlett 2009, 5, 793-797
3. Trost, B. M.; Shen, H. C.; Dong, L.; Surivet, J.-P.; Sylvain, C. J. Am. Chem. Soc. 2004, 126, 11966-11983
4. Trost, B. M.; Shen, H. C.; Dong, L.; Surivet, J.-P. J. Am. Chem. Soc. 2003, 125, 9276-9277
5. Labrosse, J.-R.; Poncet, C.; Lhoste, P.; Sinou, D. Tetrahedron: Asymmetry 1999, 10, 1069-1078
6. Welter, C.; Dahnz, A.; Brunner, B.; Streiff, S.; Dübon, P.; Helmchen, G. Org. Lett. 2005, 7, 1239-1242
7. Ito, K.; Imahayashi, Y.; Kuroda, T.; Eno, S.; Saito, B.; Katsuki, T. Tetrahedron Lett. 2004, 45, 7277-7281
8. Massacret, M.; Lakhmiri, R.; Lhoste, P.; Nguefack, C.; Abdelouahab, F. B. B.; Fadel, R.; Sinou, D. Tetrahedron: Asymmetry 2000, 11, 3561-3568
9. Massacret, M.; Lhoste, P.; Lakhmiri, R.; Parella, T.; Sinou, D. Eur. J. Org. Chem. 1999, 2665-2673
10. Lhoste, P.; Massacret, M.; Sinou, D. Bull. Soc. Chim. Fr. 1997, 134, 343-347
11. Yamazaki, A.; Achiwa, I.; Achiwa, K. Tetrahedron: Asymmetry 1996, 7, 403-406
12. Massacret, M.; Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1994, 35, 6093-6096
13. Kirsch, S. F.; Overman, L. E.; White, N. S. Org. Lett. 2007, 9, 911-913
14. Cannon, J. S.; Kirsch, S. F.; Overman, L. E.; Sneddon, H. F. J. Am. Chem. Soc. 2010, 132, 15192-15203
15. Olson, A. C.; Overman, L. E.; Sneddon, H. F.; Ziller, J. W. Adv. Synth. Catal. 2009, 351, 3186-3192
16. Stevens, A. M.; Richards, C. J. Organometallics 1999, 18, 1346-1348
17. Anderson, C. E.; Kirsch, S. F.; Overman, L. E.; Richards, C. J.; Watson, M. P. Org. Synth. 2007, 84, 148-155
18. Anderson, C. E.; Overman, L. E.; Richards, C. J.; Watson, M. P.; White, N. Org. Synth. 2007, 84, 139-147
19. Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412-12413
20. Numata, M.; Sugimoto, M.; Koike, K.; Ogawa, T. Carbohydr. Res. 1987, 163, 209-225
21. Carpenter, N. E.; Overman, L. E. In Organic Reactions; Overman, L. E., Ed.; Wiley: Hoboken, 2005; Vol. 66, pp 1-107.
22. For example, see: Meyers, C.; Maes, B. U. W.; Loones, K. T. J.; Bal, G.; Lemière, G. L. F.; Dommisse, R. A. J. Org. Chem. 2004, 69, 6010-6017
23. Keck, G. E.; Krishnamurthy, D. J. Org. Chem. 1996, 61, 7638-7639
24. McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981-3019
25. TURBOMOLE V6.2, Turbomole GmbH: Karlsruhe, Germany, 2009; http://www.turbomole.com.
26. Treutler, O.; Ahlrichs, R. J. Chem. Phys. 1995, 102, 346-354
27. Slater, J. C. Quantum Theory of Molecules and Solids, Vol. 4: The Self-Consistent Field for Molecules and Solids; McGraw-Hill: New York, 1974.
28. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211
29. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100
30. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
31. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200-206
32. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
33. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
34. Klamt, A.; Schüürmann, G. J. Chem. Soc., Perkin Trans. 2 1993, 799-805
35. Eichkorn, K.; Weigend, F.; Treutler, O.; Ahlrichs, R. Theor. Chem. Acc. 1997, 97, 119-124
36. Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829-5835
37. Weigend, F.; Furche, F.; Ahlrichs, R. J. Chem. Phys. 2003, 119, 12753-12762
38. Birch, A. J.; Maung, M.; Pelter, A. Aust. J. Chem. 1969, 22, 1923-1932
39. Mori, M.; Tonogaki, K.; Kinoshita, A. Org. Synth. 2005, 81, 1-13
40. Jones, T. K.; Denmark, S. E. Org. Synth. 1986, 64, 182-185
41. Taber, D. F.; Herr, R. J.; Gleave, D. M. J. Org. Chem. 1997, 62, 194-198
42. Brown, C. A.; Ahuja, V. K. J. Org. Chem. 1973, 38, 2226-2230
43. Davies, S. G.; Pyatt, D. J. Organomet. Chem. 1990, 387, 381-390
44. Verdaguer, X.; Berk, S. C.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 12641-12642
45. Caldwell, J. J.; Cameron, I. D.; Christie, S. D. R.; Hay, A. M.; Johnstone, C.; Kerr, W. J.; Murray, A. Synthesis 2005, 19, 3293-3296
46. Marecak, D. M.; Horiuchi, Y.; Arai, H.; Shimonaga, M.; Maki, Y.; Koyama, T.; Ogura, K.; Prestwich, G. D. Bioorg. Med. Chem. Lett. 1997, 7, 1973-1978
47. Crich, D.; Krishnamurthy, V.; Brebion, F.; Karatholuvhu, M.; Subramanian, V.; Hutton, T. K. J. Am. Chem. Soc. 2007, 129, 10282-10294
48. CYLview, 1.0b: Legault, C. Y. Université de Sherbrooke, 2009; http://www.cylview.org.