Synthetic potential of configurationally unstable chiral carbanions

Synlett

Volumn 23, Issue 15, 2012, Pages 2153-2164

  Sasaki, Michiko ^a   Takeda, Kei ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

Brook rearrangement; carbanions; nitriles; stereoselective synthesis; Wittig rearrangement

Indexed keywords

ANION; CARBANION; EPOXIDE; EPOXYSILANE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; MOLECULAR STABILITY; SOLVENT EFFECT; STEREOCHEMISTRY; SYNTHESIS; WITTIG REARRANGEMENT;

EID: 84864502515     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1290440     Document Type: Article

References (63)

1. Still WC, Sreekumar C. J. Am. Chem. Soc.: 1980; 102 1201
2. Clayden J. Organolithiums: Selectivity for Synthesis. Pergamon Oxford: 2002
3. Gawley RE. In Stereochemical Aspects of Organolithium Compounds, Topics in Stereochemistry. Vol. 26 Gawley RE, Siegel J. Chap. 3 Wiley New York: 2010; 93 133
4. Kizirian J.-C. In Stereochemical Aspects of Organolithium Compounds, Topics in Stereochemistry. Vol. 26 Gawley RE, Siegel J. Chap. 6 Wiley New York: 2010; 189 251
5. Basu A, Thayumanavan S. Angew. Chem. Int. Ed.: 2002; 41 716
6. Hoppe D, Hense T. Angew. Chem., Int. Ed. Engl.: 1997; 36 2282
7. Hoppe D. In The Chemistry of Organolithium Compounds. Vol. 1 Rappoport Z, Marek I. Wiley Chichester: 2004; 1055 1164
8. Hoppe D, Marr F, Brüggemann M. In Organolithiums in Enantioselective Synthesis. Hodgson DM. Springer New York: 2003; 61 137
9. Walborsky HM, Motes JM. J. Am. Chem. Soc.: 1970; 92 2445
10. Walborsky HM, Motes JM. J. Am. Chem. Soc.: 1970; 92 2445
11. Walborsky HM, Youssef AA, Motes JM. J. Am. Chem. Soc.: 1962; 84 2465
12. Walborsky HM, Hornyak FM. J. Am. Chem. Soc.: 1955; 77 6026
13. Carlier PR, Zhang Y. Org. Lett.: 2007; 9 1319
14. Carlier PR. Chirality: 2003; 15 340
15. Takeda K, Kawanishi E, Sasaki M, Takahashi Y, Yamaguchi K. Org. Lett.: 2002; 4 1511
16. Sasaki M, Kawanishi E, Nakai Y, Matsumoto T, Yamaguchi K, Takeda K. J. Org. Chem.: 2003; 68 9330
17. Matsumoto T, Masu H, Yamaguchi K, Takeda K. Org. Lett.: 2004; 6 4367
18. Sasaki M, Horai MTakeda K. Tetrahedron Lett.: 2006; 47 9271
19. Sasaki M, Takeda K. Org. Lett.: 2004; 6 4849
20. Tanaka K, Takeda K. Tetrahedron Lett.: 2004; 45 7859
21. Okamoto N, Sasaki M, Kawahata MYamaguchi K, Takeda K. Org. Lett.: 2006; 8 1889
22. Nakai Y, Kawahata M, Yamaguchi K, Takeda K. J. Org. Chem.: 2007; 72 1379
23. Cuadrado P, González-Nogai AM. Tetrahedron Lett.: 2000; 41 1111
24. Cuadrado P, González-Nogai AM. Tetrahedron Lett.: 1997; 38 8117
25. Nakai T, Mikami K. Chem. Rev.: 1986; 86 885
26. Marshall JA. In Comprehensive Organic Synthesis. Vol. 3 Trost BM, Fleming I. Pergamon Oxford: 1991; 975 1014
27. Mikami K, Nakai T. Synthesis: 1991; 594
28. Nakai T, Mikami K. Org. React.: 1994; 46 105
29. Nakai T, Tomooka K. Pure Appl. Chem.: 1997; 696 595
30. Hodgson DM, Tomooka K, Gras E. In Organolithiums in Enantioselective Synthesis. Hodgson DM. Springer New York: 2003; 217
31. Curtin DY, Koehl WJ. Jr. J. Am. Chem. Soc.: 1962; 84 1967
32. Wu S, Lee S, Beak P. J. Am. Chem. Soc.: 1996; 118 715
33. Carstens A, Hoppe D. Tetrahedron: 1994; 50 6097
34. Gawley RE, Zhang Q. Tetrahedron: 1994; 50 6077
35. Kapeller DC, Hammerschmidt F. J. Org. Chem.: 2009; 74 2380
36. Verner EJ, Cohen T. J. Am. Chem. Soc.: 1992; 114 375
37. Verner EJ, Cohen T. J. Org. Chem.: 1992; 57 1072
38. Hoffmann R, Brückner R. Chem. Ber.: 1992; 125 1957
39. Tomooka K, Igarashi T, Nakai T. Tetrahedron: 1994; 50 5927
40. Hoffmann R, Rückert T, Brückner R. Tetrahedron Lett.: 1993; 34 297
41. Schäfer H, Schöllkopf U, Walter D. Tetrahedron Lett.: 1968; 9 2809
42. Evans DA, Baillargeon DJ. Tetrahedron Lett.: 1978; 19 3315
43. Azzena U, Denurra T, Melloni G, Piroddi AM. J. Org. Chem.: 1990; 55 5532
44. Tomooka K, Yamamoto H, Nakai T. J. Am. Chem. Soc.: 1996; 118 3317
45. Tomooka K, Yamamoto H, Nakai T. Liebigs Ann./Recl.: 1997; 1275
46. Hoffmann RW. In Stereochemical Aspects of Organolithium Compounds, Topics in Stereochemistry. Vol. 26 Gawley RE, Siegel J. Chap. 5 Wiley New York: 2010; 165 188
47. Hoffmann RW, Lanz J, Metternich R, Tarara G, Hoppe D. Angew. Chem., Int. Ed. Engl.: 1987; 26 1145
48. Hirsch R, Hoffmann RW. Chem. Ber.: 1992; 125 975
49. Hoffmann RW, Rühl T, Harbach J. Liebigs Ann. Chem.: 1992; 725
50. Hoffmann RW, Julius M, Chemla F, Ruhland T, Frenzen G. Tetrahedron: 1994; 50 6049
51. Basu A, Gallagher D, Beak P. J. Org. Chem.: 1996; 61 5718
52. Beak P, Basu A, Gallagher DJ, Park YS, Thayumanavan S. Acc. Chem. Res.: 1996; 29 552
53. Denmark SE, Dorow RL. J. Org. Chem.: 1990; 55 5926
54. O'Brien P, Powell HR, Raithby PR, Warren S. J. Chem. Soc., Perkin Trans. 1: 1997; 1031
55. Boche G. Angew. Chem., Int. Ed. Engl.: 1989; 28 277
56. Gais H.-J, Vollhardt J, Lindner HJ. Angew. Chem., Int. Ed. Engl.: 1986; 25 939
57. Gais H.-J, Hellmann G. J. Am. Chem. Soc.: 1992; 114 4439
58. Bordwell FG. Acc. Chem. Res.: 1998; 31 456
59. Taft RW, Bordwell FG. Acc. Chem. Res.: 1998; 31 463
60. Zhang S, Zhang X.-M, Bordwell FG. J. Am. Chem. Soc.: 1995; 117 602
61. Fleming FF, Shook BC. Tetrahedron: 2002; 58 1
62. Arseniyadis S, Kyler KS, Watt DS. Org. React.: 1984; 31 1
63. Fleming FF, Gudipati S, Zhang Z, Liu W, Steward OW. J. Org. Chem.: 2005; 70 3845