Novel Reactions Starting from α-Hydroxymonothioacetals

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 55, Issue 3, 1997, Pages 217-228

  Sato, Tsuneo ^a  

^a KURASHIKI UNIVERSITY OF SCIENCE AND THE ARTS   (Japan)

Author keywords

1,3 Dicarbonyl compound; 1,4 Asymmetric induction; 1,4 Dicarbonyl compound; Acetylene; Allylic sulfide; Allylmetal; Cross coupling reaction; (Phenylthio)aldehyde; Hydroxymonothioacetal; Hydroxysulfide

Indexed keywords

ACETYLENE; ALDEHYDES; KETONES; OLEFINS; SYNTHESIS (CHEMICAL);

ALLYLIC SULFIDES; CROSS COUPLING REACTION; HYDROXYMONOTHIOACETALS; PHENYLTHIOALDEHYDES;

SULFUR COMPOUNDS;

EID: 0031102048     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.55.217     Document Type: Article

References (101)

1. B.M. Trost, C.H. Miller, J. Am. Chem. Soc., 97, 7182 (1975); T. Mandai, K. Hara, T. Nakajima, M. Kawada, J. Otera, Tetrahedron Lett., 24, 4993 (1983); J. Otera, Synthesis, 1988, 95
2. B.M. Trost, C.H. Miller, J. Am. Chem. Soc., 97, 7182 (1975); T. Mandai, K. Hara, T. Nakajima, M. Kawada, J. Otera, Tetrahedron Lett., 24, 4993 (1983); J. Otera, Synthesis, 1988, 95
3. B.M. Trost, C.H. Miller, J. Am. Chem. Soc., 97, 7182 (1975); T. Mandai, K. Hara, T. Nakajima, M. Kawada, J. Otera, Tetrahedron Lett., 24, 4993 (1983); J. Otera, Synthesis, 1988, 95
4. Heteroatom Chemistry, ed. by E. Block, VCH, New York, 1990
5. H. Nozaki, "Organometallics in Synthesis - A Manual -", ed. by M. Schlosser, John Wiley & Sons, Chichester, 1994, p.535; J. Otera, T. Sato, H. Nozaki, "Stereocontrolled Organic Synthesis", ed. by B.M. Trost, Blackwell Scientific Publications, 1994, p.117
6. H. Nozaki, "Organometallics in Synthesis - A Manual -", ed. by M. Schlosser, John Wiley & Sons, Chichester, 1994, p.535; J. Otera, T. Sato, H. Nozaki, "Stereocontrolled Organic Synthesis", ed. by B.M. Trost, Blackwell Scientific Publications, 1994, p.117
7. T. Sato, H. Okazaki, J. Otera, H. Nozaki, J. Am. Chem. Soc., 110, 5209 (1988)
8. J. Yoshida, S. Nakatani, S. Isoe, J. Org. Chem., 54, 5666 (1989); B. Boubia, C. Mioskowski, S. Manna, J.R. Falck, Tetrahedron Lett., 30, 6023 (1989); K. Chibale, S. Warren, ibid., 35, 3991 (1994); M. Makosza, M. Sypniewski, ibid., 35, 6142 (1994)
9. J. Yoshida, S. Nakatani, S. Isoe, J. Org. Chem., 54, 5666 (1989); B. Boubia, C. Mioskowski, S. Manna, J.R. Falck, Tetrahedron Lett., 30, 6023 (1989); K. Chibale, S. Warren, ibid., 35, 3991 (1994); M. Makosza, M. Sypniewski, ibid., 35, 6142 (1994)
10. J. Yoshida, S. Nakatani, S. Isoe, J. Org. Chem., 54, 5666 (1989); B. Boubia, C. Mioskowski, S. Manna, J.R. Falck, Tetrahedron Lett., 30, 6023 (1989); K. Chibale, S. Warren, ibid., 35, 3991 (1994); M. Makosza, M. Sypniewski, ibid., 35, 6142 (1994)
11. J. Yoshida, S. Nakatani, S. Isoe, J. Org. Chem., 54, 5666 (1989); B. Boubia, C. Mioskowski, S. Manna, J.R. Falck, Tetrahedron Lett., 30, 6023 (1989); K. Chibale, S. Warren, ibid., 35, 3991 (1994); M. Makosza, M. Sypniewski, ibid., 35, 6142 (1994)
12. T. Sato, J. Otera, Synlett, 1995, 351
13. M. Hannaby, S. Warren, Tetrahedron Lett., 26, 3133 (1985)
14. T. Mukaiyama, M. Imaoka, Chem. Lett., 1978, 413; W.H. Pirkle, P.L. Rinaldi, J. Org. Chem., 43, 3803 (1978)
15. T. Mukaiyama, M. Imaoka, Chem. Lett., 1978, 413; W.H. Pirkle, P.L. Rinaldi, J. Org. Chem., 43, 3803 (1978)
16. M.T. Reetz, "Organotitanium Reagents in Organic Synthesis", Springer, Berlin, 1986; M.T. Reetz, "Organometallics in Synthesis - A Manual-", ed. by M. Schlosser, John Wiley & Sons, Chichester, 1994, p. 195
17. M.T. Reetz, "Organotitanium Reagents in Organic Synthesis", Springer, Berlin, 1986; M.T. Reetz, "Organometallics in Synthesis - A Manual-", ed. by M. Schlosser, John Wiley & Sons, Chichester, 1994, p. 195
18. T. Sato, Y. Hiramura, J. Otera, H. Nozaki, Tetrahedron Lett., 30, 2821 (1989)
19. (a) D.A. Evans, G.C. Andrews, Acc. Chem. Res., 7, 147 (1974). (b) R.W. Hoffmann, Angew. Chem., Int. Ed. Engl., 18, 563 (1979)
20. (a) D.A. Evans, G.C. Andrews, Acc. Chem. Res., 7, 147 (1974). (b) R.W. Hoffmann, Angew. Chem., Int. Ed. Engl., 18, 563 (1979)
21. T. Sato, H. Okazaki, J. Otera, H. Nozaki, Tetrahedron Lett., 29, 2979 (1988); T. Sato, J. Otera, H. Nozaki, J. Org. Chem., 54, 2779 (1989); T. Sato, J. Otera, Tetrahedron Lett., 35, 6701 (1994); T. Sato, H. Shima, J. Otera, J. Org. Chem., 60, 3936 (1995); T. Cohen, W.D. Abraham, M. Myers, J. Am. Chem. Soc., 109, 7923 (1987); K. Ogura, T. Iihama, S. Kiuchi, T. Kajiki, O. Koshikawa, K. Takahashi, H. Iida, J. Org. Chem., 51, 700 (1986)
22. T. Sato, H. Okazaki, J. Otera, H. Nozaki, Tetrahedron Lett., 29, 2979 (1988); T. Sato, J. Otera, H. Nozaki, J. Org. Chem., 54, 2779 (1989); T. Sato, J. Otera, Tetrahedron Lett., 35, 6701 (1994); T. Sato, H. Shima, J. Otera, J. Org. Chem., 60, 3936 (1995); T. Cohen, W.D. Abraham, M. Myers, J. Am. Chem. Soc., 109, 7923 (1987); K. Ogura, T. Iihama, S. Kiuchi, T. Kajiki, O. Koshikawa, K. Takahashi, H. Iida, J. Org. Chem., 51, 700 (1986)
23. T. Sato, H. Okazaki, J. Otera, H. Nozaki, Tetrahedron Lett., 29, 2979 (1988); T. Sato, J. Otera, H. Nozaki, J. Org. Chem., 54, 2779 (1989); T. Sato, J. Otera, Tetrahedron Lett., 35, 6701 (1994); T. Sato, H. Shima, J. Otera, J. Org. Chem., 60, 3936 (1995); T. Cohen, W.D. Abraham, M. Myers, J. Am. Chem. Soc., 109, 7923 (1987); K. Ogura, T. Iihama, S. Kiuchi, T. Kajiki, O. Koshikawa, K. Takahashi, H. Iida, J. Org. Chem., 51, 700 (1986)
24. T. Sato, H. Okazaki, J. Otera, H. Nozaki, Tetrahedron Lett., 29, 2979 (1988); T. Sato, J. Otera, H. Nozaki, J. Org. Chem., 54, 2779 (1989); T. Sato, J. Otera, Tetrahedron Lett., 35, 6701 (1994); T. Sato, H. Shima, J. Otera, J. Org. Chem., 60, 3936 (1995); T. Cohen, W.D. Abraham, M. Myers, J. Am. Chem. Soc., 109, 7923 (1987); K. Ogura, T. Iihama, S. Kiuchi, T. Kajiki, O. Koshikawa, K. Takahashi, H. Iida, J. Org. Chem., 51, 700 (1986)
25. T. Sato, H. Okazaki, J. Otera, H. Nozaki, Tetrahedron Lett., 29, 2979 (1988); T. Sato, J. Otera, H. Nozaki, J. Org. Chem., 54, 2779 (1989); T. Sato, J. Otera, Tetrahedron Lett., 35, 6701 (1994); T. Sato, H. Shima, J. Otera, J. Org. Chem., 60, 3936 (1995); T. Cohen, W.D. Abraham, M. Myers, J. Am. Chem. Soc., 109, 7923 (1987); K. Ogura, T. Iihama, S. Kiuchi, T. Kajiki, O. Koshikawa, K. Takahashi, H. Iida, J. Org. Chem., 51, 700 (1986)
26. T. Sato, H. Okazaki, J. Otera, H. Nozaki, Tetrahedron Lett., 29, 2979 (1988); T. Sato, J. Otera, H. Nozaki, J. Org. Chem., 54, 2779 (1989); T. Sato, J. Otera, Tetrahedron Lett., 35, 6701 (1994); T. Sato, H. Shima, J. Otera, J. Org. Chem., 60, 3936 (1995); T. Cohen, W.D. Abraham, M. Myers, J. Am. Chem. Soc., 109, 7923 (1987); K. Ogura, T. Iihama, S. Kiuchi, T. Kajiki, O. Koshikawa, K. Takahashi, H. Iida, J. Org. Chem., 51, 700 (1986)
27. S.H. Pine, Org. React., 43, 1 (1993)
28. P. Brownbridge, J. Durman, P.G. Hunt, S. Warren, J. Chem. Soc., Perkin Trans. I, 1986, 1947
29. H. Stetter, H. Kuhlmann, Org. React., 40, 407 (1991)
30. T. Sato, M. Kido, J. Otera, Angew. Chem., Int. Ed. Engl., 34, 2254 (1995)
31. I. Fleming, H. Kuhne, K. Takaki, J. Chem. Soc., Perkin Trans. I, 1986, 725
32. M.T. Reetz, F. Wang, K. Harms, J. Chem. Soc., Chem. Commun., 1991, 1309
33. P. Wipf, Y. Kim, J. Am. Chem. Soc., 116, 11678 (1994); H. Dumartin, Y. LeF-loch, R. Gree, Tetrahedron Lett., 36, 6681 (1994)
34. P. Wipf, Y. Kim, J. Am. Chem. Soc., 116, 11678 (1994); H. Dumartin, Y. LeF-loch, R. Gree, Tetrahedron Lett., 36, 6681 (1994)
35. L.M. Jackman, S. Sternhell, "Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry 2nd Ed. ", Pergamon Press, Oxford, 1969, Chapter 4-2
36. A.E. Dorigo, K. Morokuma, J. Am. Chem. Soc., 111, 6524 (1989)
37. H.B. Burgi, Angew. Chem., Int. Ed. Engl., 14, 460 (1975); H.B. Burgi, J.D. Dunitz, Acc. Chem. Res., 16, 153 (1983)
38. H.B. Burgi, Angew. Chem., Int. Ed. Engl., 14, 460 (1975); H.B. Burgi, J.D. Dunitz, Acc. Chem. Res., 16, 153 (1983)
39. R. Noyori, T. Sato, H. Kobayashi, Tetrahedron Lett., 21, 2569 (1980); R. Noyori, T. Sato, H. Kobayashi, Bull. Chem. Soc. Jpn., 56, 2661 (1983)
40. R. Noyori, T. Sato, H. Kobayashi, Tetrahedron Lett., 21, 2569 (1980); R. Noyori, T. Sato, H. Kobayashi, Bull. Chem. Soc. Jpn., 56, 2661 (1983)
41. B.W. Gung, M.S. Gerdeman, R.A. Fouch, M.A. Wolf, J. Org. Chem., 59, 4255 (1994); B.W. Gung, J.P. Melnick, M.A. Wolf, A. King, ibid., 60, 1947 (1995)
42. B.W. Gung, M.S. Gerdeman, R.A. Fouch, M.A. Wolf, J. Org. Chem., 59, 4255 (1994); B.W. Gung, J.P. Melnick, M.A. Wolf, A. King, ibid., 60, 1947 (1995)
43. N.D. Epiotis, W.R. Cherry, S. Shaik, R. Tates, F. Bernardi, Top. Curr. Chem., 70, 13 (1977); A.S. Cieplak, J. Am. Chem. Soc., 103, 4540 (1981); Y.D. Wu, K.N. Houk, J. Am. Chem. Soc., 109, 908 (1987)
44. N.D. Epiotis, W.R. Cherry, S. Shaik, R. Tates, F. Bernardi, Top. Curr. Chem., 70, 13 (1977); A.S. Cieplak, J. Am. Chem. Soc., 103, 4540 (1981); Y.D. Wu, K.N. Houk, J. Am. Chem. Soc., 109, 908 (1987)
45. N.D. Epiotis, W.R. Cherry, S. Shaik, R. Tates, F. Bernardi, Top. Curr. Chem., 70, 13 (1977); A.S. Cieplak, J. Am. Chem. Soc., 103, 4540 (1981); Y.D. Wu, K.N. Houk, J. Am. Chem. Soc., 109, 908 (1987)
46. T. Sato, M. Inoue, S. Kobara, J. Otera, H. Nozaki, Tetrahedron Lett., 30, 91 (1989)
47. S. Warren, Acc. Chem. Res., 11, 401 (1978); S.G. Warren, Top. Curr. Chem., 91, 1 (1980)
48. S. Warren, Acc. Chem. Res., 11, 401 (1978); S.G. Warren, Top. Curr. Chem., 91, 1 (1980)
49. T. Mukaiyama, M. Murakami, Synthesis, 1987, 1043; A. Alexakis, P. Mangeney, Tetrahedron:Asymmetry, 1, 477(1990), S.E. Denmark, T.M. Willson, "Selectivities in Lewis Acid Promoted Reactions", ed. by D. Schinzer, Kluwer Academic Publishers, Dordrecht, 1989, Chapter 13; T. Sammakia, R.S. Smith, J. Org. Chem., 57, 2997 (1992); idem, J. Am. Chem. Soc., 114, 10998 (1992); idem, ibid., 116, 7915 (1994)
50. T. Mukaiyama, M. Murakami, Synthesis, 1987, 1043; A. Alexakis, P. Mangeney, Tetrahedron:Asymmetry, 1, 477(1990), S.E. Denmark, T.M. Willson, "Selectivities in Lewis Acid Promoted Reactions", ed. by D. Schinzer, Kluwer Academic Publishers, Dordrecht, 1989, Chapter 13; T. Sammakia, R.S. Smith, J. Org. Chem., 57, 2997 (1992); idem, J. Am. Chem. Soc., 114, 10998 (1992); idem, ibid., 116, 7915 (1994)
51. T. Mukaiyama, M. Murakami, Synthesis, 1987, 1043; A. Alexakis, P. Mangeney, Tetrahedron:Asymmetry, 1, 477(1990), S.E. Denmark, T.M. Willson, "Selectivities in Lewis Acid Promoted Reactions", ed. by D. Schinzer, Kluwer Academic Publishers, Dordrecht, 1989, Chapter 13; T. Sammakia, R.S. Smith, J. Org. Chem., 57, 2997 (1992); idem, J. Am. Chem. Soc., 114, 10998 (1992); idem, ibid., 116, 7915 (1994)
52. T. Mukaiyama, M. Murakami, Synthesis, 1987, 1043; A. Alexakis, P. Mangeney, Tetrahedron:Asymmetry, 1, 477(1990), S.E. Denmark, T.M. Willson, "Selectivities in Lewis Acid Promoted Reactions", ed. by D. Schinzer, Kluwer Academic Publishers, Dordrecht, 1989, Chapter 13; T. Sammakia, R.S. Smith, J. Org. Chem., 57, 2997 (1992); idem, J. Am. Chem. Soc., 114, 10998 (1992); idem, ibid., 116, 7915 (1994)
53. T. Mukaiyama, M. Murakami, Synthesis, 1987, 1043; A. Alexakis, P. Mangeney, Tetrahedron:Asymmetry, 1, 477(1990), S.E. Denmark, T.M. Willson, "Selectivities in Lewis Acid Promoted Reactions", ed. by D. Schinzer, Kluwer Academic Publishers, Dordrecht, 1989, Chapter 13; T. Sammakia, R.S. Smith, J. Org. Chem., 57, 2997 (1992); idem, J. Am. Chem. Soc., 114, 10998 (1992); idem, ibid., 116, 7915 (1994)
54. T. Mukaiyama, M. Murakami, Synthesis, 1987, 1043; A. Alexakis, P. Mangeney, Tetrahedron:Asymmetry, 1, 477(1990), S.E. Denmark, T.M. Willson, "Selectivities in Lewis Acid Promoted Reactions", ed. by D. Schinzer, Kluwer Academic Publishers, Dordrecht, 1989, Chapter 13; T. Sammakia, R.S. Smith, J. Org. Chem., 57, 2997 (1992); idem, J. Am. Chem. Soc., 114, 10998 (1992); idem, ibid., 116, 7915 (1994)
55. J. Eames, R.V.H. Jones, S. Warren, Tetrahedron Lett, 37, 4823 (1996)
56. Umpoled Synthons, ed. by T.A. Hase, John Wiley & Sons, New York, 1987
57. T. Sato, J. Otera, H. Nozaki, J. Org. Chem., 55, 6116 (1990)
58. R. Noyori, I. Nishida, J. Sakata, J. Am. Chem. Soc., 103, 2106 (1981)
59. Y. Yamamoto, N. Asao, Chem. Rev., 93, 2207 (1993)
60. H. Mayr, M. Patz, Angew. Chem., Int. Ed. Engl., 33, 938 (1994); M. Patz, H. Mayr, J. Bartl, S. Steenken, ibid., 34, 490 (1995)
61. H. Mayr, M. Patz, Angew. Chem., Int. Ed. Engl., 33, 938 (1994); M. Patz, H. Mayr, J. Bartl, S. Steenken, ibid., 34, 490 (1995)
62. S.E. Denmark, T. Wilson, T.M. Willson, J. Am. Chem. Soc., 110, 984 (1988); G.E. Keck, S. Castellino, M.B. Andrus, "Selectivities in Lewis Acid Promoted Reactions", ed. by D. Schinzer, Kluwer Academic Publishers, Dordrecht, 1989, p.73
63. S.E. Denmark, T. Wilson, T.M. Willson, J. Am. Chem. Soc., 110, 984 (1988); G.E. Keck, S. Castellino, M.B. Andrus, "Selectivities in Lewis Acid Promoted Reactions", ed. by D. Schinzer, Kluwer Academic Publishers, Dordrecht, 1989, p.73
64. P. Deslongchamps, "Stereoelectronic Effects in Organic Chemistry", Pergamon Press, Oxford, 1983, Chapters
65. K. Toyoshima, T. Okuyama, T. Fueno, J. Org. Chem., 43, 2789 (1978)
66. G. Capozzi, G. Modena, "Organic Sulfur Chemistry", ed. by F. Bernardi, I.G. Csizmadia, A. Mangini, Elsevier, Amsterdam, 1985, Chapter 5
67. E.L. Eliel, "Asymmetric Synthesis", Vol.2, Part A, ed. by J.D. Morrison, Academic Press, New York, 1983, Chapters 5.
68. M. Shimagaki, Y. Matsuzaki, I. Hori, T. Nakata, T. Oishi, Tetrahedron Lett., 25, 4779 (1984)
69. E. Block, "Reactions of Organosulfur Compounds", Academic Press, New York, 1978, p.132.
70. T. Sato, J. Otera, J. Organomet. Chem., 473, 55 (1994)
71. N.S. Issacs, "Physical Organic Chemistry", Longman Scientific & Technical, Essex, 1987, Chapter 10
72. I. Fleming, J. Dunogues, R. Smithers, Org. React., 37, 57 (1989)
73. T. Sato, H. Tsuchiya, J. Otera, Synlett, 1995, 628
74. T. Cohen, M. Bhupathy, Acc. Chem. Res., 22, 152 (1989); T. Cohen, "Heteroatom Chemistry", ed. by E. Block, VCH, New York, 1990, Chapter 7
75. T. Cohen, M. Bhupathy, Acc. Chem. Res., 22, 152 (1989); T. Cohen, "Heteroatom Chemistry", ed. by E. Block, VCH, New York, 1990, Chapter 7
76. [E.I. Heiba, R.M. Dessau, J. Org. Chem., 32, 3837 (1967)], D.W. Young, "Protective Groups in Organic Chemistry", ed. by J.F.W. McOmie, Plenum Press, London, 1973, Chapters 8
77. [E.I. Heiba, R.M. Dessau, J. Org. Chem., 32, 3837 (1967)], D.W. Young, "Protective Groups in Organic Chemistry", ed. by J.F.W. McOmie, Plenum Press, London, 1973, Chapters 8
78. P. Blatcher, S. Warren, J. Chem. Soc., Perkin Trans. I, 1979, 1075; D.J. Ager, ibid., 1983, 1131
79. P. Blatcher, S. Warren, J. Chem. Soc., Perkin Trans. I, 1979, 1075; D.J. Ager, ibid., 1983, 1131
80. J. E. McMurry, Chem. Rev., 89, 1513 (1989); D. Lenoir, Synthesis, 1989, 883
81. J. E. McMurry, Chem. Rev., 89, 1513 (1989); D. Lenoir, Synthesis, 1989, 883
82. D.P. Bauer, R.S. Macronber, J. Org. Chem., 41, 2640 (1976); J.E. McMurry, M.P. Fleming, K.L. Kees, L.R. Krepski, ibid., 43, 3255 (1978); L. Horner, K. Dickerhof, Chem. Ber., 116, 1615 (1983)
83. D.P. Bauer, R.S. Macronber, J. Org. Chem., 41, 2640 (1976); J.E. McMurry, M.P. Fleming, K.L. Kees, L.R. Krepski, ibid., 43, 3255 (1978); L. Horner, K. Dickerhof, Chem. Ber., 116, 1615 (1983)
84. D.P. Bauer, R.S. Macronber, J. Org. Chem., 41, 2640 (1976); J.E. McMurry, M.P. Fleming, K.L. Kees, L.R. Krepski, ibid., 43, 3255 (1978); L. Horner, K. Dickerhof, Chem. Ber., 116, 1615 (1983)