Asymmetric lithiation of 2-alkynyl aryl sulfides-Enantio- and diastereoselective formation of allenyl aryl sulfides and their application in nickel-catalyzed cross-coupling reactions

Tetrahedron Letters

Volumn 48, Issue 49, 2007, Pages 8636-8642

  Otte, Ralf ^a   Wibbeling, Birgit ^a   Fröhlich, Roland ^a   Nakamura, Shuichi ^b   Shibata, Norio ^b   Toru, Takeshi ^b   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Allenes; Asymmetric synthesis; Carbanions; Cross coupling reaction; Lithiation

Indexed keywords

ALLENYL 2 PYRIDINYL SULFIDE DERIVATIVE; LITHIUM; NICKEL; SULFIDE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; LITHIATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 36148941396     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.037     Document Type: Article

References (82)

1. For reviews, see:. Hoppe D., and Hense T. Angew. Chem. 109 (1997) 2376-2410
2. Hoppe D., and Hense T. Angew. Chem., Int. Ed. 36 (1997) 2282-2316
3. Hoppe D., Marr F., and Brüggemann M. In: Hodgson D.M. (Ed). Top. Organomet. Chem. Vol. 5 (2003), Springer, Berlin 61-137
4. Beak P., Johnson T., Kim D., and Kim S. In: Hodgson D.M. (Ed). Top. Organomet. Chem. Vol. 5 (2003), Springer, Berlin 139-176
5. Hoppe D., and Christoph G. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organolithium Compounds (2004), Wiley, Chichester 1055-1164
6. For review see:. Toru T., and Nakamura S. In: Hodgson D.M. (Ed). Top. Organomet. Chem. Vol. 5 (2003), Springer, Berlin 177-216
7. Hoffmann R.W., Rühl T., and Harbach J. Liebigs Ann. (1992) 725-730
8. Ahlbrecht H., Harbach J., Hoffmann R.W., and Ruhland T. Liebigs Ann. (1995) 211-216
9. Dress R.K., Rölle T., and Hoffmann R.W. Chem. Ber. 128 (1995) 673-677
10. Hoffmann R.W., Dress R.K., Ruhland T., and Wenzel A. Chem. Ber. 128 (1995) 861-870
11. Reich H.J., and Dykstra R.R. Angew. Chem. 105 (1993) 1489-1491
12. Reich H.J., and Dykstra R.R. Angew. Chem., Int. Ed. Engl 32 (1993) 1469-1471
13. Reich H.J., and Dykstra R.R. J. Am. Chem. Soc. 115 (1993) 7041-7042
14. Reich H.J., and Kulicke K.J. J. Am. Chem. Soc. 117 (1995) 6621-6622
15. Reich H.J., and Kulicke K.J. J. Am. Chem. Soc. 118 (1996) 273-274
16. Hoffmann R.W., Julius M., Chemla F., Ruhland T., and Frenzen G. Tetrahedron 50 (1994) 6049-6060
17. Basu A., and Thayumanavan S. Angew. Chem. 114 (2002) 740-763
18. Basu A., and Thayumanavan S. Angew. Chem., Int. Ed. 41 (2002) 716-738
19. Kaiser B., and Hoppe D. Angew. Chem. 107 (1995) 344-346
20. Kaiser B., and Hoppe D. Angew. Chem., Int. Ed. Engl. 34 (1995) 323-325
21. Hoppe D., Kaiser B., Stratmann O., and Fröhlich R. Angew. Chem. 109 (1997) 2872-2874
22. Hoppe D., Kaiser B., Stratmann O., and Fröhlich R. Angew. Chem., Int. Ed. 36 (1997) 2784-2786
23. Stratmann O., Kaiser B., Fröhlich R., Meyer O., and Hoppe D. Chem. Eur. J. 7 (2001) 423-435
24. Marr F., Fröhlich R., and Hoppe D. Org. Lett. 1 (1999) 2081-2083
25. Marr F., Fröhlich R., Wibbeling B., Diedrich C., and Hoppe D. Eur. J. Org. Chem. (2002) 2970-2988
26. Nakamura S., Nakagawa R., Watanabe Y., and Toru T. Angew. Chem. 112 (2000) 361-363
27. Nakamura S., Nakagawa R., Watanabe Y., and Toru T. Angew. Chem., Int. Ed. 39 (2000) 353-355
28. Nakamura S., Nakagawa R., Watanabe Y., and Toru T. J. Am. Chem. Soc. 122 (2000) 11340-11347
29. Nakamura S., Furutani A., and Toru T. Eur. J. Org. Chem. (2002) 1690-1695
30. For dynamic thermodynamic resolution, see:. Beak P., Anderson D.R., Curtis M.D., Laumer J.M., Pippel D.J., and Weisenburger G.A. Acc. Chem. Res. 33 (2000) 715-727
31. Park Y.S., Yum E.K., Basu A., and Beak P. Org. Lett. 8 (2006) 2667-2770
32. Clayden J., Lai L.W., and Helliwell M. Tetrahedron 60 (2004) 4399-4412
33. For dynamic kinetic resolution, see:. Noyori R., Tokunaga M., and Kitamura M. Bull. Chem. Soc. Jpn. 68 (1995) 36-55
34. Ward R.S. Tetrahedron: Asymmetry 6 (1995) 1475-1490
35. Caddick S., and Jenkins K. Chem. Soc. Rev. 25 (1996) 447-456
36. Pellissier H. Tetrahedron 59 (2003) 8291-8327
37. Nakamura S., Kato T., Nishimura H., and Toru T. Chirality 16 (2004) 86-89
38. Komine N., Wang L.-F., Tomooka K., and Nakai T. Tetrahedron Lett. 40 (1999) 6809-6812
39. Tomooka K., Wang L.-F., Komine F., and Nakai T. Tetrahedron Lett. 40 (1999) 6813-6816
40. For recent examples, see:. Nakamura S., Ito Y., Wang L., and Toru T. J. Org. Chem. 69 (2004) 1581-1589
41. Wang L., Nakamura S., Ito Y., and Toru T. Tetrahedron: Asymmetry 15 (2004) 3059-3072
42. Sonawane R.P., Fröhlich R., and Hoppe D. Adv. Synth. Catal. 348 (2006) 1847-1854
43. For the first example using catalytic amounts of bis(oxazoline) ligands, see:. Nakamura S., Hirata N., Kita T., Yamada R., Nakane D., Shibata N., and Toru T. Angew. Chem. 119 (2007) 7792-7794
44. Nakamura S., Hirata N., Kita T., Yamada R., Nakane D., Shibata N., and Toru T. Angew. Chem., Int. Ed. 46 (2007) 7648-7650
45. Hoppe D., and Riemenschneider C. Angew. Chem. 95 (1983) 64-65
46. Hoppe D., and Riemenschneider C. Angew. Chem., Int. Ed. Engl. 22 (1983) 54-55
47. Hoppe D., Gonschorrek C., Schmidt D., and Egert E. Tetrahedron 43 (1987) 2457-2466
48. Schultz-Fademrecht C., Wibbeling B., Fröhlich R., and Hoppe D. Org. Lett. 3 (2001) 1221-1224
49. Otte R., Fröhlich R., Wibbeling B., and Hoppe D. Angew. Chem. 117 (2005) 5629-5633
50. Otte R., Fröhlich R., Wibbeling B., and Hoppe D. Angew. Chem., Int. Ed. 44 (2005) 5492-5496
51. For a review on organosulfur compounds as electrophiles in transition metal-catalyzed reactions, see:. Dubbaka S.R., and Vogel P. Angew. Chem. 117 (2005) 7848-7859
52. Dubbaka S.R., and Vogel P. Angew. Chem., Int. Ed. 117 (2005) 7674-7684
53. Examples for cross-coupling reactions of organyl aryl sulfides, see:. Okamura H., Miura M., and Takei H. Tetrahedron Lett. 20 (1979) 43-46
54. Wenkert E., Ferreira T.W., and Michelotte E.L. J. Chem. Soc., Chem. Commun. (1979) 637-638
55. Wenkert E., Shepard M.E., and McPhail A.T. J. Chem. Soc., Chem. Commun. (1986) 1390-1391
56. Itami K., Mineno M., Muraoka N., and Yoshida J. J. Am. Chem. Soc. 126 (2004) 11778-11779
57. For a recent example of enantioselective synthesis of allenes by asymmetric lithiation and substitution, see:. Bou Chedid R., Brümmer M., Wibbeling B., Fröhlich R., and Hoppe D. Angew. Chem. 119 (2007) 3192-3195
58. Bou Chedid R., Brümmer M., Wibbeling B., Fröhlich R., and Hoppe D. Angew. Chem., Int. Ed. 46 (2007) 3131-3134
59. For general reviews on the synthesis of allenes, see. Hoffmann-Röder A., and Krause N. Angew. Chem. 114 (2002) 3057-3059
60. Hoffmann-Röder A., and Krause N. Angew. Chem., Int. Ed. 41 (2002) 2933-2935
61. In: Krause N., and Hashmi A.S.K. (Eds). Modern Allene Chemistry (2004), Wiley-VCH, Weinheim
62. Krause N., and Hoffmann-Röder A. Tetrahedron 60 (2004) 11671-11694
63. Brummond K.M., and DeForrest J.E. Synthesis (2007) 795-818
64. 3 using a modification of the method described by Lu:. Zhao L., Lu X., Xu W. J. Org. Chem. 70 (2005) 4059-4063
65. For the preparation of 4,4-dimethyl-but-2-yn-1-ol, see:. MacInnes I., and Walton J.C. J. Chem. Soc., Perkin Trans. 2 (1987) 1077-1082
66. An asymmetric transformation describes the conversion of a racemate into a pure enantiomer or into a mixture in which one enantiomer is present in excess, or of a diastereomeric mixture into a single diastereoisomer or into a mixture in which one diastereomer predominates. If the two enantiomers of a chiral substrate A are freely interconvertible, and if an equal amount of excess of a non-racemizing second enantiomerically pure chemical species, say (R)-B, is added to a solution of racemic A, then the resulting equilibrium mixture of adducts A·B will, in general, contain unequal amounts of diastereoisomers (R)-A·(R)-B and (S)-A·(R)-B. The result of this equilibration is called asymmetric transformation of the first kind. If, in such a system, the adducts differ considerably in solubility so that only one of them, say (R)-A·(R)-B, crystallizes from the solution, then the equilibration of diastereoisomers in solution and concurrent crystallization will continue so that all (or most) of the substrate A can be isolated as the crystalline diastereoisomer (R)-A·(R)-B. Such a 'crystallization-induced asymmetric transformation' is called an asymmetric transformation of the second kind. See. In: McNaught A.D., and Wilkinson A. (Eds). IUPAC Compendium of Chemical Terminology. 2nd ed. (1997), Blackwell Science
67. see also. Harris M.M. Progr. Stereochem. 2 (1958) 157-163
68. For the first example of an asymmetric transformation of the second kind in lithium carbanion chemistry, see:. Hoppe D., and Zschage O. Angew. Chem. 101 (1989) 67-71
69. Hoppe D., and Zschage O. Angew. Chem., Int. Ed. Engl. 28 (1989) 69-71
70. Paulsen H., Graeve C., and Hoppe D. Synthesis (1996) 141-144
71. Data sets were collected with a Nonius KappaCCD diffractometers. Programs used: data collection COLLECT (Nonius B. V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Methods in Enzymology 1997, 276, 307-326), absorption correction Denzo (Otwinowski, Z.; Borek, D.; Majewski, W.; Minor, W. Acta Crystallogr. 2003, A59, 228-234), structure solution shelxs-97 (Sheldrick, G. M.; Acta Crystallogr. 1990, A46, 467-473), structure refinement shelxl-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics SCHAKAL (Keller, E. Universität Freiburg, 1997). CCDC 656888 (11a) and CCDC 656889 (16aa) contain the supplementary crystallographic data for this Letter. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (internat.) +44 (1223) 336 033, e-mail: deposit@ccdc.cam.ac.uk].
72. -3, hydrogen atoms calculated and refined as riding atoms.
73. Seppi M., Kalkofen R., Reupohl J., Fröhlich R., and Hoppe D. Angew. Chem. 116 (2004) 1447-1451
74. Seppi M., Kalkofen R., Reupohl J., Fröhlich R., and Hoppe D. Angew. Chem., Int. Ed. 43 (2004) 1423-1427
75. 3 over a period of 10 min compared to the addition at once) showed no evidence for dynamic kinetic resolution.
76. The corresponding titanated S-2-alkynyl thiocarbamates and O-2-alkynyl carbamates 2 are configurationally stable at -78 °C.
77. 3 up to 4 h.
78. 16b failed.
79. The configuration of the double bond was determined by NOE-experiments.
80. Erdik E. Tetrahedron 43 (1987) 2203-2212
81. NMR analysis of the crude product gave no hints for the existence or non-existence of a second diastereomer.
82. -3, hydrogen atoms calculated and refined as riding atoms.