On the effect of tether composition on cisltrans selectivity in intramolecular diels-alder reactions

Chemistry - An Asian Journal

Volumn 4, Issue 1, 2009, Pages 126-134

  Paddon Row, Michael N ^a   Longshaw, Alistair I ^b   Willis, Anthony C ^b   Sherburn, Michael S ^b  

^a UNIVERSITY OF NEW SOUTH WALES   (Australia)

^b AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

Cycloaddition; Density functional calculations; Diastereoselectivity; Tether groups; Transition structures

Indexed keywords

CARBONYL GROUPS; CBS-QB3; DENSITY FUNCTIONAL CALCULATIONS; DIASTEREOSELECTIVITY; DIELS-ALDER REACTIONS; EXPERIMENTAL VERIFICATIONS; HOLD UP; IMDA REACTIONS; LOCAL PLANARITY; METHYLENE GROUPS; ORBITAL INTERACTIONS; PRODUCT RATIOS; RELATIVE ENERGIES; SYSTEMATIC TRENDS; TETHER GROUPS; THIOAMIDE; TRANSITION STRUCTURES;

CHEMICAL BONDS; CHEMICAL REACTIONS; ELECTROCHEMICAL PROPERTIES; ELECTRONEGATIVITY; ESTERS; EXPERIMENTS; FLOW INTERACTIONS; ISOMERS; OPTICAL COMMUNICATION; STEREOSELECTIVITY;

TETHERLINES;

EID: 58149178730     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200800352     Document Type: Article

References (70)

1. IMDA Reviews: a) D. F. Taber, Intramolecular Diels-Alder and Aider Ene Reactions, Springer, Berlin, 1984;
2. b) A. G. Fallis, Can. J. Chem. 1984, 62, 183-234;
3. c) E. Ciganek, Org. React. 1984, 32, 1-374;
4. d) D. Craig. Chem. Soc. Rev. 1987, 16, 187-238;
5. e) W. R. Roush in Advances in Cycloaddition, Vol. 2 (Ed.: D. P. Curran). JAI, Greenwich, CT. 1990, pp. 91-146;
6. f) W. R. Roush in Comprehensive Organic Synthesis. Vol.5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, pp. 513-550;
7. g) T. Oh, M. Reilly, Org. Prep. Proced. Int. 1994. 26, 129-158;
8. h) D. Craig in Methods of Organic Chemistry (Houben-Weyl) 4th ed.. Vol. E21c (Eds.: Q Helmchen, R. W. Hoffmann, J. Mulzer, E. Schumann), Thieme, Stuttgart, 1995. pp. 2872-2904:
9. i) A. G. Fallis, Acc. Chem. Res. 1999, 32, 464-474;
10. j) B. R. Bear, S. M. Sparks, K. J. Shea. Angew. Chem. 2001, 113, 864-894;
11. Angew. Chem. Int. Ed. 2001, 40, 820-849:
12. k) E. Marsault. A. Toro, P. Nowak, P. Deslongchamps. Tetrahedron 2001, 57, 4243-4260;
13. l) K.-i. Takao. R. Munakata, K.-i. Tadano, Chem. Rev. 2005, 105, 4779-4807.
14. M. J. Lilly. M. N. Paddon-Row, M. S. Sherburn, C. I. Turner, Chem. Commun. 2000, 2213-2214.
15. M.N. Paddon-Row. M.S. Sherburn, Chem. Commun. 2000, 2215-2216.
16. C. I. Turner, R. M. Williamson, M. N. Paddon-Row, M. S. Sherburn, J. Org. Chem. 2001, 66, 3963-3969.
17. T. N. Cayzer, L. S.-M. Wong, P. Turner, M. N. Paddon-Row, M. S. Sherburn, Chem. Eur. J. 2002, 8, 739-750.
18. G. A. Jones, M. N. Paddon-Row, M. S. Sherburn, C. I. Turner. Org. Lett. 2002, 4, 3789-3792.
19. C. I. Turner. R. M. Williamson, P. Turner, M. S. Sherburn. Chem. Commun. 2003, 1610-1611.
20. T. N. Cayzer, M. N. Paddon-Row, M. S. Sherburn. Eur. J. Org. Chem. 2003, 4059-4068.
21. C. I. Turner, M. N. Paddon-Row. A. C. Willis, M. S. Sherburn, J. Org. Chem. 2005, 70, 1154-1163.
22. M. J. Lilly, N. A. Miller, A. J. Edwards. A. C. Willis, P. Turner, M. N. Paddon-Row, M. S. Sherburn, Chem. Eur. J. 2005, 11, 2525-2536.
23. T. N. Cayzer, M.J. Lilly, R. M. Williamson, M.N. Paddon-Row, M. S. Sherburn, Org. Biomol. Chem. 2005, 3, 1302-1307.
24. T. N. Cayzer, M.N. Paddon-Row, D. Moran, A.D. Payne, M.S. Sherburn, P. Turner, J. Org. Chem. 2005, 70, 5561-5570.
25. M. N. Paddon-Row, D. Moran, G. A. Jones, M.S. Sherburn. J. Org. Chem. 2005, 70, 10841-10853.
26. T. N. Cayzer, N. A. Miller. M. N. Paddon-Row, M. S. Sherburn, Org. Biomol. Chem. 2006, 4, 2019-2024.
27. E. L. Pearson, L. C. H. Kwan, C. I. Turner, G. A. Jones. A. C. Willis, M. N. Paddon-Row, M. S. Sherburn, J. Org. Chem. 2006, 71, 6099-6109.
28. R. Tripoli, T. N. Cayzer. A. C. Willis, M. S. Sherburn, M. N. PaddonRow, Org. Biomol. Chem. 2007, 5, 2606-2616.
29. E. L. Pearson, A. C. Willis, M. S. Sherburn, M. N. Paddon-Row, Org. Biomol. Chem. 2008, 6, 513-522.
30. M. N. Paddon-Row, L. C. H. Kwan, A.C. Willis, M.S. Sherburn, Angew. Chem. 2008, 120, 7121-7125;
31. Angew. Chem. Int. Ed. 2008, 47, 7013-7017.
32. For clarity, we employ a product-based nomenclature to distinguish the stereochemistry of the two IMDA TSs, depicted in Scheme 1.
33. All reactants are identified by a number and their IMDA TSs and products are given the same number, followed by the suffix TS and P, respectively.
34. F. K. Brown. K. N. Houk, Tetrahedron Lett. 1985, 26, 2297-2300.
35. Y.-T. Lin, K. N. Houk, Tetrahedron Lett. 1985, 26, 2269-2272.
36. L. Raimondi, F. K. Brown, J. Gonzalez, K. N. Houk, J. Am. Chem. Soc. 1992, 114, 4796-4804.
37. a) A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100:
38. b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37. 785-789;
39. c) P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627.
40. W. J. Hehre, L. Radom, P. v. R. Schleyer. J. A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York, 1986.
41. The Encyclopedia of Computational Chemistry (Eds.: P. v. R. Schleyer, N. L. Allinger, T. Clark. J. Gasteiger, P. A. Kollman, H. F. Schaefer III, P. R. Schreiner), Wiley, Chichester, 1998.
42. D.J. Tantillo, K. N. Houk, M. E. Jung, J. Org. Chem. 2001, 66, 1938-1940.
43. O. Wiest, D. C. Montiel, K. N. Houk, J. Phys. Chem. A 1997, 101, 8378-8388.
44. a) J. A. Montgomery, Jr., M. J. Frisch, J. W. Ochterski. G. A. Petersson, J. Chem. Phys. 1999, 110, 2822-2827:
45. b) J. A. Montgomery, Jr., M. J. Frisch, J. W. Ochterski, G. A. Petersson, J. Chem. Phys. 2000, 112, 6532-6542.
46. a) M. R. Nyden, G. A. Pelersson, J. Chem. Phys. 1981, 75, 1843-1862;
47. b) G. A. Pelersson, M. A. Al-Laham, J. Chem. Phys. 1991, 94, 6081-6090;
48. c) G. A. Petersson, T. G. Tensfeldt, J. A. Montgomery.Jr., J. Chem. Phys. 1991, 94, 6091-6101;
49. d) G. A. Petersson, K. Malick, W. G. Wilson, J. W. Ochterski, J. A. Montgomery, Jr., M. J. Frisch, J. Chem. Phys. 1998, 109, 10570-10579.
50. S.N. Pieniazek, K.N. Houk, Angew. Chem. 2006, 118, 1470-1473;
51. Angew. Chem. Int. Ed. 2006, 45, 1442-1445.
52. J. W. Moore, R. G. Pearson, Kinetics and Mechanism, 3rd ed.. Wiley, New York, 1981, chap. 7.
53. Gaussian 98, Revision A.11, M. J. Frisch. G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr.. R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain. O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe. P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh PA, 2001.
54. Gaussian 2003. Version B, M. J. Frisch, J. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Pelersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda. J. Hasegawa. M. lshida, T. Nakajima. Y. Honda, O. Kitao, H. Nakai. M. Klene, X. Li. J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski. P. Y. Ayala, K. Morokuma, G. A. Voth. R Salvador. J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick. A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Pittsburgh. PA, 2003.
55. We have verified this result using the value calculated for r, in either cis or trans IMDA TS at the B3LYP/6-31 +G(d) level of theory.
56. -1 higher in energy than the most stable C-H/C-H staggered (C=CZC-H eclipsed) conformation. Higher homologues lacking a Z-substituent exhibit similar behavior: E. L. EHeI, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, pp. 615-616.
57. R. B. Woodward, R. Hoffmann, The Conservation of Orbital Symmetry, Verlag Chemie. Weinheim, 1970.
58. D. A. Singleton, J. Am. Chem. Soc. 1992, 114, 6563-6564.
59. J. I. Garcia, J. A. Mayoral, L. Salvatella, Acc. Chem. Res. 2000, 33, 658-664.
60. S. Kong, J. D. Evanseck, J. Am. Chem. Soc. 2000, 122, 10418-10427.
61. Whether SOIs are important in Diels-Alder reactions remains controversial. For more detailed discussion on this issue, including evidence suggesting that SOIs are not the origin of endo selectivity in iwermolecular Diels-Alder reactions, see Ref. [39] and: a) J. I. Garcia, M. Martínez-Merino, J. A. Mayoral, L. Salvatella, J. Am. Chem. Soc. 1998, 120, 2415-2420;
62. b) J. I. García, J. A. Mayoral, L. Salvatella, Tetrahedron 1997, 53, 6057-6064;
63. c) J. I. García, J. A. Mayoral, L. Salvatella, Eur. J. Org. Chem. 2005, 85-90.
64. R. Hertel, J. Mattay, J. Runsink, J. Am. Chem. Soc. 1991, 113, 657-665.
65. D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877-4880.
66. 2Ph and N-Ph derivatives of 5 give synthetic cisltrans cycloadduct ratios of 50:50 and 60:40, respectively, in refluxing toluene: J. M. Mellor, A.M. Wagland, J. Chem. Soc. Perkin Trans. 1 1989, 997-1005. Our results are in excellent agreement with these findings.
67. See the Supporting Information for full experimental details.
68. J. B. Foresman, M. Frisch. Exploring Chemistry with Electronic Structure Methods, 2nd. ed., Gaussian, Inc., Pittsburgh. 1996.
69. O. Acevedo. J. D. Evansek, Org. Lett. 2003, 5, 649-652.
70. Gschwend et al. report the exclusive formation of the frans-cycloadduct from the 1,2-diphenyl-9-E-carbomethoxy analogue of 14. whereas the corresponding acrylamide furnished a 50:50 mixture of ws- and trans-fused products: H. W. Gschwend, A. O. Lee, H. P. Meier, J. Org. Chem. 1973, 38, 2169-2175.