Regio- and Stereoselective Syntheses with Organocopper Reagents

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 3, 1997, Pages 186-204

  Krause, Norbert ^a   Gerold, Andreas ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Catalysis; Chirality; Copper reagents; Synthetic methods

Indexed keywords

EID: 0030902124     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199701861     Document Type: Review

References (239)

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11. Review: a) J. F. Normant, A. Alexakis, Synthesis 1981, 841-870; b) E. Erdik, Tetrahedron 1984, 40, 641-657; c) R. J. K. Taylor, Synthesis 1985, 364-392; d) Y. Yamamoto, Angew. Chem. 1986, 98, 945-957; Angew. Chem. Int. Ed. Engl. 1986, 25, 947-959; e) B. H. Lipshutz, Synthesis 1987, 325-341; f) Synlett 1990, 119-128; g) E. Nakamura, ibid. 1991, 539-547; h) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; i) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992; j) Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford, 1994; k) B. H. Lipshutz in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley, Chichester, 1994, pp. 283-382; l) N. Krause, Metallorganische Chemie, Spektrum Akademischer Verlag, Heidelberg, 1996, pp. 175-200; m) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
12. Review: a) J. F. Normant, A. Alexakis, Synthesis 1981, 841-870; b) E. Erdik, Tetrahedron 1984, 40, 641-657; c) R. J. K. Taylor, Synthesis 1985, 364-392; d) Y. Yamamoto, Angew. Chem. 1986, 98, 945-957; Angew. Chem. Int. Ed. Engl. 1986, 25, 947-959; e) B. H. Lipshutz, Synthesis 1987, 325-341; f) Synlett 1990, 119-128; g) E. Nakamura, ibid. 1991, 539-547; h) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; i) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992; j) Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford, 1994; k) B. H. Lipshutz in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley, Chichester, 1994, pp. 283-382; l) N. Krause, Metallorganische Chemie, Spektrum Akademischer Verlag, Heidelberg, 1996, pp. 175-200; m) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
13. Review: a) J. F. Normant, A. Alexakis, Synthesis 1981, 841-870; b) E. Erdik, Tetrahedron 1984, 40, 641-657; c) R. J. K. Taylor, Synthesis 1985, 364-392; d) Y. Yamamoto, Angew. Chem. 1986, 98, 945-957; Angew. Chem. Int. Ed. Engl. 1986, 25, 947-959; e) B. H. Lipshutz, Synthesis 1987, 325-341; f) Synlett 1990, 119-128; g) E. Nakamura, ibid. 1991, 539-547; h) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; i) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992; j) Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford, 1994; k) B. H. Lipshutz in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley, Chichester, 1994, pp. 283-382; l) N. Krause, Metallorganische Chemie, Spektrum Akademischer Verlag, Heidelberg, 1996, pp. 175-200; m) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
14. Review: a) J. F. Normant, A. Alexakis, Synthesis 1981, 841-870; b) E. Erdik, Tetrahedron 1984, 40, 641-657; c) R. J. K. Taylor, Synthesis 1985, 364-392; d) Y. Yamamoto, Angew. Chem. 1986, 98, 945-957; Angew. Chem. Int. Ed. Engl. 1986, 25, 947-959; e) B. H. Lipshutz, Synthesis 1987, 325-341; f) Synlett 1990, 119-128; g) E. Nakamura, ibid. 1991, 539-547; h) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; i) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992; j) Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford, 1994; k) B. H. Lipshutz in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley, Chichester, 1994, pp. 283-382; l) N. Krause, Metallorganische Chemie, Spektrum Akademischer Verlag, Heidelberg, 1996, pp. 175-200; m) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
15. Review: a) J. F. Normant, A. Alexakis, Synthesis 1981, 841-870; b) E. Erdik, Tetrahedron 1984, 40, 641-657; c) R. J. K. Taylor, Synthesis 1985, 364-392; d) Y. Yamamoto, Angew. Chem. 1986, 98, 945-957; Angew. Chem. Int. Ed. Engl. 1986, 25, 947-959; e) B. H. Lipshutz, Synthesis 1987, 325-341; f) Synlett 1990, 119-128; g) E. Nakamura, ibid. 1991, 539-547; h) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; i) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992; j) Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford, 1994; k) B. H. Lipshutz in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley, Chichester, 1994, pp. 283-382; l) N. Krause, Metallorganische Chemie, Spektrum Akademischer Verlag, Heidelberg, 1996, pp. 175-200; m) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
16. Review: a) J. F. Normant, A. Alexakis, Synthesis 1981, 841-870; b) E. Erdik, Tetrahedron 1984, 40, 641-657; c) R. J. K. Taylor, Synthesis 1985, 364-392; d) Y. Yamamoto, Angew. Chem. 1986, 98, 945-957; Angew. Chem. Int. Ed. Engl. 1986, 25, 947-959; e) B. H. Lipshutz, Synthesis 1987, 325-341; f) Synlett 1990, 119-128; g) E. Nakamura, ibid. 1991, 539-547; h) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; i) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992; j) Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford, 1994; k) B. H. Lipshutz in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley, Chichester, 1994, pp. 283-382; l) N. Krause, Metallorganische Chemie, Spektrum Akademischer Verlag, Heidelberg, 1996, pp. 175-200; m) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
17. Review: a) J. F. Normant, A. Alexakis, Synthesis 1981, 841-870; b) E. Erdik, Tetrahedron 1984, 40, 641-657; c) R. J. K. Taylor, Synthesis 1985, 364-392; d) Y. Yamamoto, Angew. Chem. 1986, 98, 945-957; Angew. Chem. Int. Ed. Engl. 1986, 25, 947-959; e) B. H. Lipshutz, Synthesis 1987, 325-341; f) Synlett 1990, 119-128; g) E. Nakamura, ibid. 1991, 539-547; h) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; i) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992; j) Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford, 1994; k) B. H. Lipshutz in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley, Chichester, 1994, pp. 283-382; l) N. Krause, Metallorganische Chemie, Spektrum Akademischer Verlag, Heidelberg, 1996, pp. 175-200; m) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
18. Review: a) J. F. Normant, A. Alexakis, Synthesis 1981, 841-870; b) E. Erdik, Tetrahedron 1984, 40, 641-657; c) R. J. K. Taylor, Synthesis 1985, 364-392; d) Y. Yamamoto, Angew. Chem. 1986, 98, 945-957; Angew. Chem. Int. Ed. Engl. 1986, 25, 947-959; e) B. H. Lipshutz, Synthesis 1987, 325-341; f) Synlett 1990, 119-128; g) E. Nakamura, ibid. 1991, 539-547; h) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; i) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992; j) Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford, 1994; k) B. H. Lipshutz in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley, Chichester, 1994, pp. 283-382; l) N. Krause, Metallorganische Chemie, Spektrum Akademischer Verlag, Heidelberg, 1996, pp. 175-200; m) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
19. Review: a) J. F. Normant, A. Alexakis, Synthesis 1981, 841-870; b) E. Erdik, Tetrahedron 1984, 40, 641-657; c) R. J. K. Taylor, Synthesis 1985, 364-392; d) Y. Yamamoto, Angew. Chem. 1986, 98, 945-957; Angew. Chem. Int. Ed. Engl. 1986, 25, 947-959; e) B. H. Lipshutz, Synthesis 1987, 325-341; f) Synlett 1990, 119-128; g) E. Nakamura, ibid. 1991, 539-547; h) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; i) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992; j) Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford, 1994; k) B. H. Lipshutz in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley, Chichester, 1994, pp. 283-382; l) N. Krause, Metallorganische Chemie, Spektrum Akademischer Verlag, Heidelberg, 1996, pp. 175-200; m) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
20. Review: a) J. F. Normant, A. Alexakis, Synthesis 1981, 841-870; b) E. Erdik, Tetrahedron 1984, 40, 641-657; c) R. J. K. Taylor, Synthesis 1985, 364-392; d) Y. Yamamoto, Angew. Chem. 1986, 98, 945-957; Angew. Chem. Int. Ed. Engl. 1986, 25, 947-959; e) B. H. Lipshutz, Synthesis 1987, 325-341; f) Synlett 1990, 119-128; g) E. Nakamura, ibid. 1991, 539-547; h) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; i) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992; j) Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford, 1994; k) B. H. Lipshutz in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley, Chichester, 1994, pp. 283-382; l) N. Krause, Metallorganische Chemie, Spektrum Akademischer Verlag, Heidelberg, 1996, pp. 175-200; m) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
21. Review: a) J. F. Normant, A. Alexakis, Synthesis 1981, 841-870; b) E. Erdik, Tetrahedron 1984, 40, 641-657; c) R. J. K. Taylor, Synthesis 1985, 364-392; d) Y. Yamamoto, Angew. Chem. 1986, 98, 945-957; Angew. Chem. Int. Ed. Engl. 1986, 25, 947-959; e) B. H. Lipshutz, Synthesis 1987, 325-341; f) Synlett 1990, 119-128; g) E. Nakamura, ibid. 1991, 539-547; h) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; i) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992; j) Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford, 1994; k) B. H. Lipshutz in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley, Chichester, 1994, pp. 283-382; l) N. Krause, Metallorganische Chemie, Spektrum Akademischer Verlag, Heidelberg, 1996, pp. 175-200; m) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
22. Review: a) J. F. Normant, A. Alexakis, Synthesis 1981, 841-870; b) E. Erdik, Tetrahedron 1984, 40, 641-657; c) R. J. K. Taylor, Synthesis 1985, 364-392; d) Y. Yamamoto, Angew. Chem. 1986, 98, 945-957; Angew. Chem. Int. Ed. Engl. 1986, 25, 947-959; e) B. H. Lipshutz, Synthesis 1987, 325-341; f) Synlett 1990, 119-128; g) E. Nakamura, ibid. 1991, 539-547; h) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; i) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992; j) Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford, 1994; k) B. H. Lipshutz in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley, Chichester, 1994, pp. 283-382; l) N. Krause, Metallorganische Chemie, Spektrum Akademischer Verlag, Heidelberg, 1996, pp. 175-200; m) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
23. Review: a) J. F. Normant, A. Alexakis, Synthesis 1981, 841-870; b) E. Erdik, Tetrahedron 1984, 40, 641-657; c) R. J. K. Taylor, Synthesis 1985, 364-392; d) Y. Yamamoto, Angew. Chem. 1986, 98, 945-957; Angew. Chem. Int. Ed. Engl. 1986, 25, 947-959; e) B. H. Lipshutz, Synthesis 1987, 325-341; f) Synlett 1990, 119-128; g) E. Nakamura, ibid. 1991, 539-547; h) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; i) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992; j) Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford, 1994; k) B. H. Lipshutz in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley, Chichester, 1994, pp. 283-382; l) N. Krause, Metallorganische Chemie, Spektrum Akademischer Verlag, Heidelberg, 1996, pp. 175-200; m) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
24. Review: a) J. F. Normant, A. Alexakis, Synthesis 1981, 841-870; b) E. Erdik, Tetrahedron 1984, 40, 641-657; c) R. J. K. Taylor, Synthesis 1985, 364-392; d) Y. Yamamoto, Angew. Chem. 1986, 98, 945-957; Angew. Chem. Int. Ed. Engl. 1986, 25, 947-959; e) B. H. Lipshutz, Synthesis 1987, 325-341; f) Synlett 1990, 119-128; g) E. Nakamura, ibid. 1991, 539-547; h) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; i) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992; j) Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford, 1994; k) B. H. Lipshutz in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley, Chichester, 1994, pp. 283-382; l) N. Krause, Metallorganische Chemie, Spektrum Akademischer Verlag, Heidelberg, 1996, pp. 175-200; m) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
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29. a) E. Piers, R. D. Tillyer, J. Org. Chem. 1988, 53, 5366-5369;
30. b) B. H. Lipshutz, D. C. Reuter, E. L. Ellsworth, ibid. 1989, 54, 4975-4977;
31. c) B. H. Lipshutz, S. Sharma, D. C. Reuter, Tetrahedron Lett. 1990, 31, 7253-7256;
32. d) J. P. Marino, M. V. M. Emonds, P. J. Stengel, A. R. M. Oliveira, F. Simonelli, J. T. B. Ferreira, ibid. 1992, 33, 49-52;
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35. Review: P. Wipf, Synthesis 1993, 537-557.
36. a) M. Arai, E. Nakamura, B. H. Lipshutz, J. Org. Chem. 1991, 56, 5489-5491;
37. b) M. Arai, B. H. Lipshutz, E. Nakamura, Tetrahedron 1992, 48, 5709-5718.
38. a) B. H. Lipshutz, E. L. Ellsworth, J. Am. Chem. Soc. 1990, 112, 7440-7441;
39. b) B. H. Lipshutz, K. Kato, Tetrahedron Lett. 1991, 32, 5647-5650;
40. c) L. M. Venanzi, R. Lehmann, R. Keil, B. H. Lipshutz, ibid. 1992, 33, 5857-5860;
41. d) B. H. Lipshutz, R. Keil, J. Am. Chem. Soc. 1992, 114, 7919-7920;
42. e) B. H. Lipshutz, M. R. Wood, ibid. 1993, 115, 12625-12626;
43. f) ibid. 1994, 116, 11 689-11 702;
44. g) Tetrahedron Lett. 1994, 35, 6433-6436;
45. h) P. Wipf, J. H. Smitrovich, J. Org. Chem. 1991, 56, 6494-6496.
46. a) R. E. Ireland, P. Wipf, J. Org. Chem. 1990, 55, 1425-1426;
47. b) B. H. Lipshutz, S. H. Dimock, ibid. 1991, 56, 5761-5763;
48. c) P. Wipf, J. H. Smitrovich, C.-W. Moon, ibid. 1992, 57, 3178-3186;
49. d) J. Westermann, K. Nickisch, Angew. Chem. 1993, 105, 1429-1431; Angew. Chem. Int. Ed. Engl. 1993, 32, 1368-1370.
50. d) J. Westermann, K. Nickisch, Angew. Chem. 1993, 105, 1429-1431; Angew. Chem. Int. Ed. Engl. 1993, 32, 1368-1370.
51. a) J. R. Behling, K. A. Babiak, J. S. Ng, A. L. Campbell, R. Moretti, M. Koerner, B. H. Lipshutz, J. Am. Chem. Soc. 1988, 110, 2641-2643;
52. b) B. H. Lipshutz, R. Crow, S. H. Dimock, E. L. Ellsworth, R. A. J. Smith, J. R. Behling, ibid. 1990, 112, 4063-4064;
53. c) B. H. Lipshutz, C. Ung, T. R. Elworthy, D. C. Reuter, Tetrahedron Lett. 1990, 31, 4539-4542;
54. d) B. H. Lipshutz, J. I. Lee, ibid. 1991, 32, 7211-7214;
55. e) R. K. Dieter, C. W. Alexander, Synlett 1993, 407-409.
56. a) Y. Tamaru, H. Ochiai, T. Nakamura, Z. Yoshida, Angew. Chem. 1987, 99, 1193-1195; Angew. Chem. Int. Ed. Engl. 1987, 26, 1157-1159;
57. a) Y. Tamaru, H. Ochiai, T. Nakamura, Z. Yoshida, Angew. Chem. 1987, 99, 1193-1195; Angew. Chem. Int. Ed. Engl. 1987, 26, 1157-1159;
58. b) E. Nakamura, S. Aoki, K. Sekiya, H. Oshino, I. Kuwajima, J. Am. Chem. Soc. 1987, 109, 8056-8066;
59. c) M. T. Crimmins, P. G. Nantermet, J. Org. Chem. 1990, 55, 4235-4237;
60. d) M. T. Crimmins, P. G. Nantermet, B. W. Trotter, I. M. Vallin, P. S. Watson, L. A. McKerlie, T. L. Reinhold, A. W. H. Cheung, K. A. Stetson, D. Dedopoulou, J. L. Gray, ibid. 1993, 58, 1038-1047;
61. e) Y. Yamamoto, Y. Chounan, M. Tanaka, T. Ibuka, ibid. 1992, 57, 1024-1026;
62. f) T. Ibuka, K. Nakai, H. Habashita, Y. Hotta, N. Fujii, N. Mimura, Y. Miwa, T. Taga, Y. Yamamoto, Angew. Chem. 1994, 106, 693-695; Angew. Chem. Int. Ed. Engl. 1994, 33, 652-654;
63. f) T. Ibuka, K. Nakai, H. Habashita, Y. Hotta, N. Fujii, N. Mimura, Y. Miwa, T. Taga, Y. Yamamoto, Angew. Chem. 1994, 106, 693-695; Angew. Chem. Int. Ed. Engl. 1994, 33, 652-654;
64. g) A. Alexakis, J. Frutos, P. Mangeney, Tetrahedron: Asymmetry 1993, 4, 2427-2430;
65. h) B. H. Lipshutz, M. R. Wood, R. Tirado, J. Am. Chem. Soc. 1995, 117, 6126-6127.
66. Reviews: a) P. Knochel, M. J. Rozema, C. E. Tucker, C. Retherford, M. Furlong, S. A. Rao, Pure Appl. Chem. 1992, 64, 361-369; b) P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117-2188; c) P. Knochel, Synlett 1995, 393-403.
67. Reviews: a) P. Knochel, M. J. Rozema, C. E. Tucker, C. Retherford, M. Furlong, S. A. Rao, Pure Appl. Chem. 1992, 64, 361-369; b) P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117-2188; c) P. Knochel, Synlett 1995, 393-403.
68. Reviews: a) P. Knochel, M. J. Rozema, C. E. Tucker, C. Retherford, M. Furlong, S. A. Rao, Pure Appl. Chem. 1992, 64, 361-369; b) P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117-2188; c) P. Knochel, Synlett 1995, 393-403.
69. a) R. D. Rieke, Science 1989, 246, 1260-1264 (review);
70. b) R. M. Wehmeyer, R. D. Rieke, ibid. 1987, 52, 5056-5057;
71. c) T.-C. Wu, R. M. Wehmeyer, R. D. Rieke, ibid. 1987, 52, 5057-5059;
72. d) G. W. Ebert, R. D. Rieke, ibid. 1988, 53, 4482-4488;
73. e) T.-C. Wu, R. D. Rieke, Tetrahedron Lett. 1988, 29, 6753-6756;
74. f) L. Zhu, R. M. Wehmeyer, R. D. Rieke, J. Org. Chem. 1991, 56, 1445-1453;
75. g) D. E. Stack, B. T. Dawson, R. D. Rieke, J. Am. Chem. Soc. 1991, 113, 4672-4673;
76. h) G. W. Ebert, W. R. Klein, J. Org. Chem. 1991, 56, 4744-4747;
77. i) D. E. Stack, B. T. Dawson, R. D. Rieke, J. Am. Chem. Soc. 1992, 114, 5110-5116;
78. j) R. D. Rieke, D. E. Stack, B. T. Dawson, T.-C. Wu, J. Org. Chem. 1993, 58, 2483-2491;
79. k) R. D. Rieke, W. R. Klein, T.-C. Wu, ibid. 1993, 58, 2492-2500;
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185. more recent applications: a) E. Urban, G. Riehs, G. Knühl, Tetrahedron Lett. 1995, 36, 4773-4776; b) E. Urban, G. Knühl, G. Helmchen, ibid. 1995, 36, 7229-7232; c) G. Riehs, E. Urban, ibid. 1995, 36, 7233-7236.
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198. In contrast to compounds containing stereogenic centers, allenes are racemized simply by the cleavage of a π-bond. This can take place either by electrophilic attack or by catalysis with organometallic compounds (for example organocopper compounds) [41]. Allenic dioxanones of type 111 (and the corresponding enolates) are also racemized at higher temperatures by cuprates or protonic acids. (N. Krause, U. Wecker, unpublished results).
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231. III intermediates: a) R. Fernandez de la Pradilla, M. B. Rubio, J. P. Marino, A. Viso, Tetrahedron Lett. 1992, 33, 4985-4988; b) M. H. Nantz, D. M. Bender, S. Janaki, Synthesis 1993, 577-578; c) Y. Chounan, T. Ibuka, Y. Yamamoto, J. Chem. Soc. Chem. Commun. 1994, 2003-2004.
232. III intermediates: a) R. Fernandez de la Pradilla, M. B. Rubio, J. P. Marino, A. Viso, Tetrahedron Lett. 1992, 33, 4985-4988; b) M. H. Nantz, D. M. Bender, S. Janaki, Synthesis 1993, 577-578; c) Y. Chounan, T. Ibuka, Y. Yamamoto, J. Chem. Soc. Chem. Commun. 1994, 2003-2004.
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239. A. Gerold, R. Wagner, N. Krause, unpublished results.