Configurational control of benzyl carbanion-copper complexes by sulfinyl groups: Synthesis of optically pure allenes with central and axial chirality

Angewandte Chemie - International Edition

Volumn 47, Issue 36, 2008, Pages 6836-6839

  Ruano, José Luis García ^a   Marcos, Vanesa ^a   Alemán, José ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Allenes; Chirality; Copper; Sulfinyl groups; Synthetic methods

Indexed keywords

BROMINE COMPOUNDS; COPPER; COPPER COMPOUNDS; STEREOCHEMISTRY; STEREOSELECTIVITY;

ALLENES; CHIRALITY; SULFINYL GROUPS; SYNTHETIC METHODS;

COMPLEXATION;

ALKADIENE; ALLENE; ANION; CARBON; COPPER;

ARTICLE; CHEMISTRY; CONFORMATION; SYNTHESIS;

ALKADIENES; ANIONS; CARBON; COPPER; MOLECULAR CONFORMATION;

EID: 52449102093     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200802158     Document Type: Article

References (68)

1. a) B. S. Burton, H. V. Pechman, Ber. Dtsch. Chem. Ges. 1887, 20, 145;
2. b) The Chemistry of Ketenes, allenes and related compounds (Ed.: I. Patai), Wiley, New York, 1980;
3. c) The chemistry of allenes (Ed.: S. R. Landor), Academic Press. London, 1984;
4. d) A. Hoffman-Röder, N. Krause, Angew. Chem. 2004, 116, 1216;
5. Angew. Chem. Int. Ed. 2004, 43, 1196;
6. e) Modern Allene Chemistry (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004;
7. f) S. Ma, Chem. Rev. 2005, 105, 2829;
8. g) Special Volume in Cumulenes and Allenes, Vol. 44 (Eds: N. Krause), Houben-Weyl-Georg Thieme Verlar KG, Stuttgart, 2008.
9. For examples, see: a) J. Meinwald, K. Erickson, Tetrahedron Lett. 1968, 9, 2959;
10. b) R. Bonnett, A. K. Mallams, J. Chem. Soc. Chem. Commun. 1966, 515;
11. c) T. E. Deville, S. W. Russell, J. Chem. Soc. Chem. Commun. 1969, 754;
12. d) T. E. Deville, B. C. Russell, J. Chem. Soc. Chem. Commun. 1969, 1311;
13. e) J. Meinwald, L. Hendry, Tetrahedron Lett. 1969, 10, 1657;
14. f) B. C. Weedon, S. W. Russell, J. Chem. Soc. Chem. Commun. 1969, 85;
15. g) D. F. Horler, J. Chem. Soc. 1970, 859;
16. h) K. Mori, Tetrahedron Lett. 1973, 14, 723;
17. i) K. Mori, Tetrahedron 1974, 30, 1065;
18. j) W. H. Pirkle, C. W. Boeder, J. Org. Chem. 1978, 43, 2091;
19. k) P. Baret, E. Barreiro, Tetrahedron 1979, 35, 1533;
20. l) K. Mori, T. Nukada, T. Ebata, Tetrahedron 1981, 37, 1343;
21. m) A. P. Roszkowski, G. L. Garay, J. Pharmacol. Exp. Ther. 1986, 239, 382;
22. n) H. Carpio, G. F. Cooper, J. H. Edwards, Prostaglandins 1987, 33, 169;
23. o) R. M. Eglen, B. Whiting, J. Pharmacol. 1989, 98, 1335;
24. p) M. Ito, Y. Yamano, Pure Appl. Chem. 1994, 66, 939;
25. q) P. W. Collins, S. W. Djuric, Chem. Rev. 1993, 93, 1533;
26. r) N. Krause, A. Hoffman-Röder, J. Canisius, Synthesis 2000, 1759;
27. s) T. Satoh, N. Hanaki, Y. Kuramochi, Tetrahedron 2002, 58, 2533.
28. a) P. Rona, P. Crabbe, J. Am. Chem. Soc. 1968, 90, 4733;
29. b) P. Rona, P. Crabbe, J. Am. Chem. Soc. 1969, 91, 3289:
30. N2′ reactions: c) A. Alexakis, P. Mangeney, Pure Appl. Chem. 1988, 60, 49;
31. d) A. Alexakis, Pure Appl. Chem. 1992, 64, 387;
32. e) E. Erdik, Tetrahedron Lett. 1992, 48, 9577;
33. f) S. W. Djuric, M. Miyano, Tetrahedron Lett. 1987, 28, 299;
34. g) J. Mattay, M. Conrads, Synthesis 1988, 595;
35. Using sulfonates: h) D. Bernard, A. Doutheau, Tetrahedron 1987, 43, 2721;
36. i) I. Gridnev, G. Canai, J. Organomet. Chem. 1994, 481;
37. j) C. Agami, F. Couty, Tetrahedron 2000, 56, 367;
38. k) R. Danheiser, Y. Tsai, Org. Synth. Coll. Vol. 1993, 8, 471;
39. using ethers: l) I. Marek, P. Mangeney, A. Alexakis, Tetrahedron Lett. 1986, 27, 5499;
40. m) A. Alexakis, I. Marek, J. Am. Chem. Soc. 1990, 112, 8042;
41. n) I. Marek, A. Alexakis, P. Mangeney, Bull. Soc. Chim. Fr. 1992, 129, 171;
42. using halides: o) J. Burton, G. Hartgraves, Tetrahedron Lett. 1990, 31, 3699;
43. p) M. Hung, Tetrahedron Lett. 1990, 31, 3703;
44. q) M. Yus, J. Gomis, Eur. J. Org. Chem. 2003, 2043.
45. Using epoxides: r) F. Chemla, F. Ferreira, Curr. Org. Chem. 2002, 6, 539;
46. s) C. Cahiez, A. Alexakis, Synthesis 1978, 528;
47. t) J. Tigchelaar, J. Meijer, H. Kleijn, J. Organomet. Chem. 1981, 221, 117;
48. u) A. Doutheau, A. Saba, J. Gore, Tetrahedron Lett. 1982, 23, 2461;
49. using aziridines: v) H. Ohno, A. Toda, Y. Miwa, T. Taga, Tetrahedron Lett. 1999, 40, 349;
50. w) H. Ohno, A. Toda, N. Fujii, Tetrahedron 2000, 56, 2811.
51. For the synthesis of propargylic alcohols by CBS reduction, see: a) E. J. Corey, C. J. Helal, Angew. Chem. 1998, 110, 2092;
52. Angew. Chem. Int. Ed. 1998, 37, 1986.
53. For enzymatic kinetic resolution, see: b) J. A. Marshall, H. Chobanian, Org. Synth. 2005, 82, 43;
54. c) For addition of alkynyl/zinc reagents to aldehydes, see: D. E. Frantz, R. Faessler, E. M. Carreira, J. Am. Chem. Soc. 2000, 122, 1806.
55. The [Cu] notation indicates that the ligand/copper ratio is not known.
56. a) J. L. García Ruano, M. C. Carreño, M. A. Toledo, J. M. Aguirre, M. T. Aranda, J. Fischer, Angew. Chem. 2000, 112, 2848;
57. Angew. Chem. Int. Ed. 2000, 39, 2736;
58. b) J. L. García Ruano, J. Alemán, J. , M. Aranda, M. A. Fernández-Ibáñez, M. A. M. Rodríguez- Fernández, C. Maestro, Tetrahedron 2004, 60, 10067.
59. a) J. L. García Ruano, J. Alemán, F. Soriano, Org. Lett. 2003, 5, 677;
60. b) J. L. García Ruano, J. Alemán, Org. Lett. 2003, 5, 4513;
61. c) J. L. García Ruano, J. Alemán, A. Parra, J. Am. Chem. Soc. 2005, 127, 13048;
62. d) J. L. García Ruano, J. Alemán, M. B. Cid, Synthesis 2006, 687.
63. J. L. García Ruano, J. Alemán, I. Alonso, A. Parra, V. Marcos, J. Aguirre, Chem. Eur. J. 2007, 13, 6179.
64. J. L. García Ruano, M. T. Aranda, M. Puente, Tetrahedron 2005, 61, 10099.
65. For reaction with silicon reagents in a Pummerer reaction, see: a) J. L. García Ruano, J. Alemán, M. Aranda, M. J. Arévalo, A. Padwa, Org. Lett. 2005, 7, 19;
66. For reactions with tin reagents, see: b) J. L. García Ruano, J. Alemán, A. Padwa, Org. Lett. 2004, 6, 1757.
67. Racemization of the optically pure propargylic mesylate was confirmed by dissolving (R)-2 f or (S)-2 f in THF containing lithiumdiisopropyl amide. Longer reaction times did not improve the extent of dynamic kinetic resolution.
68. K. Inagaki, T. Ohta, K. Nozaki, H. Takaya, J. Organomet. Chem. 1997, 531, 159.