A case of anti carbolithiation of alkynes resulting from intramolecular lithium coordination

Chemistry - A European Journal

Volumn 14, Issue 17, 2008, Pages 5159-5167

  Fressigné, Catherine ^a,b   Girard, Anne Lise ^a   Durandetti, Muriel ^a   Maddaluno, Jacques ^a  

^a UNIVERSITÉ ET INSA DE ROUEN   (France)

^b LABORATOIRE DE CHIMIE THÉORIQUE   (France)

Author keywords

Alkynes; Carbolithiation; Cyclization; Density functional calculations; Stereoselectivity

Indexed keywords

ACETYLENE; ATOMIC PHYSICS; ATOMS; COORDINATION REACTIONS; CYCLIZATION; DISCRETE FOURIER TRANSFORMS; ETHERS; HYDROCARBONS; OLEFINS; ORGANIC COMPOUNDS; OXYGEN; PROBABILITY DENSITY FUNCTION; SULFUR COMPOUNDS;

ALKYNES; CARBOLITHIATION; DENSITY FUNCTIONAL CALCULATIONS; STEREOSELECTIVITY;

LITHIUM;

EID: 53849094109     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200701834     Document Type: Article

References (50)

1. a) F. Le Stral, J. Maddaluno, Org. Lett. 2002, 4, 2791-2793;
2. b) F. Le Strat, D. C. Harrowven. J. Maddaluno. J. Org. Chem. 2005, 70, 489-498.
3. a) W. F. Bailey, T. V. Ovaska, T. K. Leipert. Tetrahedron Lett. 1989, 30, 3901-3904;
4. b) W. F. Bailey, TV. Ovaska. J. Am. Chem. Soc. 1993, 115, 3080-3090;
5. c) W. F. Bailey, N. M. Wachler-Jurcsak, M. R. Pineau, T. V. Ovaska. R. R. Warren, C. E. Lewis, J. Org. Chem. 1996, 61, 8216-8228.
6. See, for instance: a) M. J. Mealy, W. F. Bailey, J. Organomet. Chem. 2002, 646, 59-67;
7. b) I. Marek, N. Chinkov. D. Banon-Tenne in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich. A. deMeijere) Wiley-VCH. Stuttgart. 2004, Chapter 7, pp. 395-478:
8. c) F. J. Fañanás, R. Sanz in The Chemistry of Organolithium Compounds (Eds.: Z. Rappoport, I. Marek), Vol.2, Wiley, Chichester, 2006, Chapter 4, pp. 295-379;
9. d) R. Sanz, J. M. Ignacio. M. A. Rodriguez, F. J. Fañanás, J. Barluenga, Chem. Eur. J. 2007, 13, 4998-5008.
10. W. F. Bailey. P. H. Aspris, J. Org. Chem. 1995, 60, 754-757.
11. See, for instance: a) G. Boche, M. Schimeczek, J. Cioslowski, P. Piskorz, Eur. J. Org. Chem. 1998, 1851-1860;
12. b) K. B. Wilberg, S. Sklenac, W. F. Bailey, J. Org. Chem. 2000, 65, 2014-2021;
13. c) K. Ando, J. Org. Chem. 2006, 71, 1837-1850. For a recent in-depth experimental study see also:
14. d) W. F. Bailey, M. R. Luderer, K. P. Jordan, J. Org. Chem. 2006, 71, 2825-2828.
15. E. Nakamura, M. Nakamura, Y. Miyachi, N. Koga, K. Morokuma, J. Am. Chem. Soc. 1993, 115, 99-106.
16. E. Nakamura, Y. Miyachi, N. Koga, K. Morokuma, J. Am. Chem. Soc. 1992, 114, 6686-6692.
17. W. F. Bailey, A. D. Khanolkar, K. Gavaskar, T. V. Ovaska, K. Rossi, Y. Thiel, K. B. Wilberg, J. Am. Chem. Soc. 1991, 113, 5720-5727.
18. W. F. Bailey, M. J. Mealy. K. B. Wilberg, Org. Lett. 2002, 4, 791-794.
19. See, for instance: a) C. Fressigné, J. Maddaluno, A. Marquez, C. Giessner-Preltre, J. Org. Chem. 2000, 65, 8899-8907;
20. b) L. M. Pratt, N. V. Nguyên, B. Ramachandran, J. Org. Chem. 2005, 70, 4279-_4283;
21. c) C. Fressigné, A. Lautrette, J. Maddaluno, J. Org. Chem. 2005, 70, 7816-7828.
22. Jaguar 5.0, release 22, Schrödinger, LLC. Portland, OR, 2002.
23. a) B. Silvi, A. Savin, Nature 1994, 371, 683-686;
24. b) A. Savin, B. Silvi, F. Colonna, Can. J. Chem. 1996, 74, 1088-1096. For a review, see:
25. c) A. Savin, R. Nesper, S. Wengert, T. F. Fässler. Angew. Chem. 1997, 109, 1892-1918:
26. Angew. Chem. Int. Ed. Eng. 1997, 36, 1808-1832.
27. C. Fressigné, J. Maddaluno, C. Giessner-Prettre, B. Silvi, J. Org. Chem. 2001, 66, 6476-6479.
28. a) D. B. Chesnut, J. Phys. Chem. A 2000, 104, 11644-11650;
29. b) D. B. Chesnut, J. Phys. Chem. A 2003, 107, 4307-4313;
30. c) E. Matito, J. Poater, F. M. Bickelhaupt, M. Sola, J. Phys. Chem. B 2006, 110, 7189-7198.
31. C. Fressigné, A.-L. Girard, M. Durandetti, J. Maddaluno, Angew. Chem. 2008, 120, 905-907;
32. Angew. Chem. Int. Ed. 2008, 47, 891-893.
33. Note however that the anti isomers that result from the isomerization of the original syn product were observed when the resulting vinyllithium was stabilized. See reference [2] and a) W. Bauer, M. Feigel, G. Müller, P. von R. Schleyer, J. Am. Chem. Soc. 1988, 110, 6033-6046;
34. b) N. F. McKinley, D. F. O'Shea, J. Org. Chem. 2006, 71, 9552-9555.
35. F. Le Strat, J. Maddaluno, Tetrahedron Lett. 2000, 41, 5367-5371.
36. W. F. Bailey, J. J. Patricia. J. Organomet. Chem. 1988, 352, 1-46.
37. W. Bauer, C. Griesinger, J. Am. Chem. Soc. 1993, 115, 10871-10882.
38. See. for instance reference [2a] and G. Gralla, B. Wibbeling, D. Hoppe, Org. Lett. 2002, 4, 2193-2195.
39. See. for instance: a) W. F. Bailey. T. V. Ovaska, Tetrahedron Lett. 1990, 31, 627-630;
40. b) W. F. Bailey, T. V. Ovaska, J. Am. Chem. Soc. 1993, 115, 3080-3090;
41. c) X. Wei, R. J. K. Taylor. Tetrahedron Lett. 2003, 44, 7143-7146.
42. D. J. Tannor, B. Marten, R. Murphy, R. A. Friesner, D. Sitkoff, A. Nicholls, N. Ringnalda, W. A. Goddard III, B. Honig, J. Am. Chem. Soc. 1994, 116, 11875-11882.
43. See. for instance: a) L. M. Pratt, Bull. Chem. Soc. Jpn. 2005, 78, 890-898;
44. b) Y. Yuan, S. Desjardins. A. Harrison-Marchand, H. Oulyadi, C. Fressigné. C. Giessner-Prettre. J. Maddaluno, Tetrahedron 2005, 61, 3325-3334;
45. c) L. M. Pratt, D. G. Truhlar, C. J. Cramer, S. R. Kass, J. D. Thompson, J. D. Xidos, J. Org. Chem. 2007, 72, 2962-2966.
46. Gaussian 98 (Revision A5), M. J. Frisch, G. W. Trucks. H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman. V. G. Zakrzewfki, J. A. Montgomery, 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, F. Clifford, J. Ochterski. G. A. Petersson. P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, 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, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian Inc., Pittsburgh PA, 1998.
47. It is well-known that the lone pair of a free pyramidal carbanion does not necessarily face its counterion. For a spectacular example that involves a monomeric organolithium compound, see: F. Breher, J. Grunenberg, S. C. Lawrence, P. Mountford. H. Rüegger, Angew. Chem. 2004, 116, 2575-2578:
48. Angew. Chem. Int. Ed. 2004, 43, 2521-2524.
49. A continuum solvent effect can be used to describe reactivity problems in organolithium chemistry very well: T Balle, M. Begtrup, J. W. Jaroszewski, T. Liljefors, R-O. Norrby. Org. Biomol. Chem. 2006, 4, 1261-1267.
50. Y. Yamamoto, J. Org. Chem. 2007, 72, 7817-7831.