Tandem [1,5]-H shift/6π-electrocyclizations of ketenimines bearing 1,3-oxathiane units. Computational assessment of the experimental diastereoselection

Tetrahedron

Volumn 68, Issue 24, 2012, Pages 4672-4681

  Alajarin, Mateo ^a   Bonillo, Baltasar ^a   Marin Luna, Marta ^a   Sanchez Andrada, Pilar ^b   Vidal, Angel ^a   Orenes, Raul Angel ^a  

^a UNIVERSITY OF MURCIA   (Spain)

^b Santiago de la Ribera   (Spain)

Author keywords

1,3 Oxathiane; DFT study; electrocyclization; Hydride migration; Ketenimine

Indexed keywords

IMINE; KETENE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; CYCLIZATION; DIASTEREOISOMER; ELECTROCHEMISTRY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 84861223448     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.04.021     Document Type: Article

References (56)

1. S. Kobayashi, and K.A. Jorgensen Cycloaddition Reactions in Organic Synthesis 2002 Wiley-VCH Weinheim
2. D. Enders, M. Knopp, and R. Schiffers Tetrahedron: Asymmetry 7 1996 1847 1882
3. T. Nakai, and K. Mikami Chem. Rev. 86 1986 885 902
4. E.A. Llardi, C.E. Stivala, and A. Zakarian Chem. Soc. Rev. 38 2009 3133 3148
5. K. Neuschuetz, J. Velker, and R. Neier Synthesis 1998 227 255
6. L.F. Tietze, and U. Beifuss Angew. Chem., Int. Ed. Engl. 32 1993 131 163
7. T.-L. Ho Tandem Organic Reactions 1992 Wiley New York, NY
8. L.F. Tietze, G. Brasche, and K. Gericke Domino Reactions in Organic Synthesis 2006 Wiley-VCH Weinheim
9. P.J. Parsons, C.S. Penkett, and A.J. Shell Chem. Rev. 96 1996 195 206
10. H. Pellisier Tetrahedron 62 2006 1619 1665
11. X.Y. Mak, A.L. Crombie, and R.L. Danheiser J. Org. Chem. 76 2011 1852 1873
12. J.M. Robinson, T. Sakai, K. Okano, T. Kitawaki, and R.L. Danheiser J. Am. Chem. Soc. 132 2010 11039 11041
13. A. Beck, L. Knothe, D. Hunkler, and H. Prinzbach Tetrahedron Lett. 25 1984 1785 1788
14. S.A. Raw, and R.J.K. Taylor J. Am. Chem. Soc. 126 2004 12260 12261
15. S.E. Denmark, and L. Gomez J. Org. Chem. 68 2003 8015 8024
16. H. Hopf, and J. Wolff Eur. J. Org. Chem. 2001 4009 4030
17. S.E. Denmark, and L. Gomez Org. Lett. 3 2001 2907 2910
18. T.M. Swarbrick, I. Marko, and L. Kennard Tetrahedron Lett. 32 1991 2549 2552
19. D. Skropeta, and R.W. Rickardd Tetrahedron Lett. 48 2007 3281 3284
20. K.C. Nicolaou, D.J. Edmonds, and P.G. Bulger Angew. Chem., Int. Ed. 45 2006 7134 7186
21. S. Arns, and L. Barriault Chem. Commun. 2007 2211 2221
22. M. Alajarin, B. Bonillo, M.-M. Ortin, P. Sanchez-Andrada, and A. Vidal Org. Lett. 8 2006 5645 5648
23. M. Alajarin, B. Bonillo, M.-M. Ortin, P. Sanchez-Andrada, and A. Vidal Eur. J. Org. Chem. 2011 1896 1913
24. M. Alajarin, B. Bonillo, M.-M. Ortin, P. Sanchez-Andrada, A. Vidal, and R.-A. Orenes Org. Biomol. Chem. 8 2010 4690 4700
25. W.H.N. Nijhuis, W. Verboom, D.N. Reinhoudt, and S. Harkema J. Am. Chem. Soc. 109 1987 3136 3138
26. K. Mori, S. Sueoka, and T. Akiyama J. Am. Chem. Soc. 133 2011 2424 2426
27. G. Zhou, and J. Zhang Chem. Commun. 2010 6593 6595
28. J. Barluenga, M. Fañanas-Mastral, F. Aznar, and C. Valdes Angew. Chem., Int. Ed. 47 2008 6594 6597
29. B. Bolte, and F. Gagosz J. Am. Chem. Soc. 133 2011 7696 7699
30. M.C. Haibach, I. Deb, C.K. De, and D. Seidel J. Am. Chem. Soc. 133 2011 2100 2103
31. P.A. Vadola, and D. Sames J. Am. Chem. Soc. 131 2009 16525 16528
32. M. Alajarin, B. Bonillo, P. Sanchez-Andrada, A. Vidal, and D. Bautista Org. Lett. 11 2009 1365 1368
33. M. Alajarin, B. Bonillo, P. Sanchez-Andrada, and A. Vidal J. Org. Chem. 75 2010 3737 3750
34. N.G. Rondan, and K.N. Houk J. Am. Chem. Soc. 107 1985 2099 2111
35. K. Ruldolf, D.C. Spellmeyer, and K.N. Houk J. Org. Chem. 52 1987 3708 3710
36. D.C. Spellmeyer, and K.N. Houk J. Am. Chem. Soc. 110 1988 3412 3416
37. K.N. Houk, D.C. Spellmeyer, C.W. Jefford, C.G. Rimbault, Y. Wang, and R.D. Miller J. Org. Chem. 53 1988 2125 2127
38. A.B. Buda, Y. Wang, and K.N. Houk J. Org. Chem. 54 1989 2264 2266
39. E.A. Kallel, Y. Wang, D.C. Spellmeyer, and K.N. Houk J. Am. Chem. Soc. 112 1990 6759 6763
40. N.S. Isaacs Physical Organic Chemistry 1987 Longman Scientific & Technical Belfast
41. Y. Naruse, and S. Inagaki Chem. Lett. 36 2007 820 825
42. S. Inagaki Top. Curr. Chem. 289 2009 83 127
43. H. Ikeda, N. Ushioda, and S. Inagaki Chem. Lett. 30 2001 270 271
44. M. Yasui, Y. Naruse, and S. Inagaki J. Org. Chem. 69 2004 7246 7249
45. Y. Naruse, Y. Hayashi, and S. Inagaki Tetrahedron Lett. 44 2003 8509 8512
46. J. Rodriguez-Otero J. Org. Chem. 64 1999 6842 6848
47. H. Jiao, and P.v.R. Schleyer J. Am. Chem. Soc. 117 1995 11529 11535
48. J.D. Evanseck, B.E. Thomas IV, D.C. Spellmeyer, and K.N. Houk J. Org. Chem. 60 1995 7134 7141
49. C.W. Jefford, G. Bernardinelli, Y. Wang, D.C. Spellmeyer, A. Buda, and K.N. Houk J. Am. Chem. Soc. 114 1992 1157 1165
50. J.E. Baldwin, V.P. Reddy, L.J. Schaad, and B.A. Hess J. Am. Chem. Soc. 110 1988 8554 8555
51. It is known that conjugating substituents produce large accelerations of the rate of nucleophilic additions to heterocumulenes such as ketenes, see T.T. Tidwel Ketenes 1995 Jonh Wiley & Sons New York, NY
52. J.H. Espenson Chemical Kinetics and Reaction Mechanisms 1981 McGraw-Hill New York, NY
53. M.A. Ardakani, R.K. Smalley, and R.H. Smith J. Chem. Soc., Perkin Trans. 1 1983 2501 2506
54. Prepared following the experimental procedure reported for the preparation of similar compounds in J.C. Cuevas, J. De Mendoza, and P. Prados J. Org. Chem. 53 1988 2055 2066
55. E.C. Taylor, A. McKillop, and G.H. Hawks Org. Synth. 52 1972 36 38
56. H. Pracejus, and G. Wallura J. Prakt. Chem. 19 1962 33 36