Stereospecific ring-opening reaction of epoxy sulfides with phenylboronic acid via episulfonium ions

Tetrahedron Letters

Volumn 40, Issue 16, 1999, Pages 3191-3194

  Hayakawa, Hiroyuki ^a   Okada, Naoko ^a   Miyashita, Masaaki ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENEBORONIC ACID; EPISULFONIUM ION; EPOXIDE; EPOXY SULFIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033574460     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00412-8     Document Type: Article

References (24)

1. 1 G. H. Posner, Org. React. (N. Y.), 1975, 22, 253; P. Ma, V. S. Martin, S. Masamune, K. B.Sharpless, and S. M. Viti, J. Org. Chem., 1982, 47, 1378; T. Suzuki, H. Saimoto, H. Tomioka, K. Oshima, and H. Nozaki, Tetrahedron Lett., 1982, 23, 3597; B. H. Lipshutz, R. S.Wilhelm, J. A. Kozlowski, and D. Parker, J. Org. Chem., 1984, 49, 3928; C. H. Behrens and K. B. Sharpless, ibid., 1985, 50, 5696; M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J.chem. Soc. Chem. Commun., 1988, 1173; M. Caron, P. R. Carlier, and K. B. Sharpless, J.org. Chem., 1988, 53, 5185; Comprehensive Organic Synthesis, Ed., B. M. Trost, Vol. 3, "Carbon-Carbon σ-Bond Formation", Ed., G. Pattenden, Pergamon Press (1991); C. Boniniand G. Righi, Synthesis, 1994, 225.
2. G. H. Posner, Org. React. (N. Y.), 1975, 22, 253; P. Ma, V. S. Martin, S. Masamune, K. B. Sharpless, and S. M. Viti, J. Org. Chem., 1982, 47, 1378; T. Suzuki, H. Saimoto, H. Tomioka, K. Oshima, and H. Nozaki, Tetrahedron Lett., 1982, 23, 3597; B. H. Lipshutz, R. S.Wilhelm, J. A. Kozlowski, and D. Parker, J. Org. Chem., 1984, 49, 3928; C. H. Behrens and K. B. Sharpless, ibid., 1985, 50, 5696; M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J.chem. Soc. Chem. Commun., 1988, 1173; M. Caron, P. R. Carlier, and K. B. Sharpless, J.org. Chem., 1988, 53, 5185; Comprehensive Organic Synthesis, Ed., B. M. Trost, Vol. 3, "Carbon-Carbon σ-Bond Formation", Ed., G. Pattenden, Pergamon Press (1991); C. Boniniand G. Righi, Synthesis, 1994, 225.
3. G. H. Posner, Org. React. (N. Y.), 1975, 22, 253; P. Ma, V. S. Martin, S. Masamune, K. B.Sharpless, and S. M. Viti, J. Org. Chem., 1982, 47, 1378; T. Suzuki, H. Saimoto, H. Tomioka, K. Oshima, and H. Nozaki, Tetrahedron Lett., 1982, 23, 3597; B. H. Lipshutz, R. S.Wilhelm, J. A. Kozlowski, and D. Parker, J. Org. Chem., 1984, 49, 3928; C. H. Behrens and K. B. Sharpless, ibid., 1985, 50, 5696; M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J.chem. Soc. Chem. Commun., 1988, 1173; M. Caron, P. R. Carlier, and K. B. Sharpless, J.org. Chem., 1988, 53, 5185; Comprehensive Organic Synthesis, Ed., B. M. Trost, Vol. 3, "Carbon-Carbon σ-Bond Formation", Ed., G. Pattenden, Pergamon Press (1991); C. Boniniand G. Righi, Synthesis, 1994, 225.
4. G. H. Posner, Org. React. (N. Y.), 1975, 22, 253; P. Ma, V. S. Martin, S. Masamune, K. B.Sharpless, and S. M. Viti, J. Org. Chem., 1982, 47, 1378; T. Suzuki, H. Saimoto, H. Tomioka, K. Oshima, and H. Nozaki, Tetrahedron Lett., 1982, 23, 3597; B. H. Lipshutz, R. S. Wilhelm, J. A. Kozlowski, and D. Parker, J. Org. Chem., 1984, 49, 3928; C. H. Behrens and K. B. Sharpless, ibid., 1985, 50, 5696; M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J.chem. Soc. Chem. Commun., 1988, 1173; M. Caron, P. R. Carlier, and K. B. Sharpless, J.org. Chem., 1988, 53, 5185; Comprehensive Organic Synthesis, Ed., B. M. Trost, Vol. 3, "Carbon-Carbon σ-Bond Formation", Ed., G. Pattenden, Pergamon Press (1991); C. Boniniand G. Righi, Synthesis, 1994, 225.
5. G. H. Posner, Org. React. (N. Y.), 1975, 22, 253; P. Ma, V. S. Martin, S. Masamune, K. B.Sharpless, and S. M. Viti, J. Org. Chem., 1982, 47, 1378; T. Suzuki, H. Saimoto, H. Tomioka, K. Oshima, and H. Nozaki, Tetrahedron Lett., 1982, 23, 3597; B. H. Lipshutz, R. S.Wilhelm, J. A. Kozlowski, and D. Parker, J. Org. Chem., 1984, 49, 3928; C. H. Behrens and K. B. Sharpless, ibid., 1985, 50, 5696; M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J.chem. Soc. Chem. Commun., 1988, 1173; M. Caron, P. R. Carlier, and K. B. Sharpless, J.org. Chem., 1988, 53, 5185; Comprehensive Organic Synthesis, Ed., B. M. Trost, Vol. 3, "Carbon-Carbon σ-Bond Formation", Ed., G. Pattenden, Pergamon Press (1991); C. Boniniand G. Righi, Synthesis, 1994, 225.
6. G. H. Posner, Org. React. (N. Y.), 1975, 22, 253; P. Ma, V. S. Martin, S. Masamune, K. B.Sharpless, and S. M. Viti, J. Org. Chem., 1982, 47, 1378; T. Suzuki, H. Saimoto, H. Tomioka, K. Oshima, and H. Nozaki, Tetrahedron Lett., 1982, 23, 3597; B. H. Lipshutz, R. S.Wilhelm, J. A. Kozlowski, and D. Parker, J. Org. Chem., 1984, 49, 3928; C. H. Behrens and K. B. Sharpless, ibid., 1985, 50, 5696; M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J. Chem. Soc. Chem. Commun., 1988, 1173; M. Caron, P. R. Carlier, and K. B. Sharpless, J.org. Chem., 1988, 53, 5185; Comprehensive Organic Synthesis, Ed., B. M. Trost, Vol. 3, "Carbon-Carbon σ-Bond Formation", Ed., G. Pattenden, Pergamon Press (1991); C. Boniniand G. Righi, Synthesis, 1994, 225.
7. G. H. Posner, Org. React. (N. Y.), 1975, 22, 253; P. Ma, V. S. Martin, S. Masamune, K. B.Sharpless, and S. M. Viti, J. Org. Chem., 1982, 47, 1378; T. Suzuki, H. Saimoto, H. Tomioka, K. Oshima, and H. Nozaki, Tetrahedron Lett., 1982, 23, 3597; B. H. Lipshutz, R. S.Wilhelm, J. A. Kozlowski, and D. Parker, J. Org. Chem., 1984, 49, 3928; C. H. Behrens and K. B. Sharpless, ibid., 1985, 50, 5696; M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J.chem. Soc. Chem. Commun., 1988, 1173; M. Caron, P. R. Carlier, and K. B. Sharpless, J. Org. Chem., 1988, 53, 5185; Comprehensive Organic Synthesis, Ed., B. M. Trost, Vol. 3, "Carbon-Carbon σ-Bond Formation", Ed., G. Pattenden, Pergamon Press (1991); C. Boniniand G. Righi, Synthesis, 1994, 225.
8. G. H. Posner, Org. React. (N. Y.), 1975, 22, 253; P. Ma, V. S. Martin, S. Masamune, K. B.Sharpless, and S. M. Viti, J. Org. Chem., 1982, 47, 1378; T. Suzuki, H. Saimoto, H. Tomioka, K. Oshima, and H. Nozaki, Tetrahedron Lett., 1982, 23, 3597; B. H. Lipshutz, R. S.Wilhelm, J. A. Kozlowski, and D. Parker, J. Org. Chem., 1984, 49, 3928; C. H. Behrens and K. B. Sharpless, ibid., 1985, 50, 5696; M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J.chem. Soc. Chem. Commun., 1988, 1173; M. Caron, P. R. Carlier, and K. B. Sharpless, J.org. Chem., 1988, 53, 5185; Comprehensive Organic Synthesis, Ed., B. M. Trost, Vol. 3, "Carbon-Carbon σ-Bond Formation", Ed., G. Pattenden, Pergamon Press (1991); C. Boniniand G. Righi, Synthesis, 1994, 225.
9. G. H. Posner, Org. React. (N. Y.), 1975, 22, 253; P. Ma, V. S. Martin, S. Masamune, K. B.Sharpless, and S. M. Viti, J. Org. Chem., 1982, 47, 1378; T. Suzuki, H. Saimoto, H. Tomioka, K. Oshima, and H. Nozaki, Tetrahedron Lett., 1982, 23, 3597; B. H. Lipshutz, R. S.Wilhelm, J. A. Kozlowski, and D. Parker, J. Org. Chem., 1984, 49, 3928; C. H. Behrens and K. B. Sharpless, ibid., 1985, 50, 5696; M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J.chem. Soc. Chem. Commun., 1988, 1173; M. Caron, P. R. Carlier, and K. B. Sharpless, J.org. Chem., 1988, 53, 5185; Comprehensive Organic Synthesis, Ed., B. M. Trost, Vol. 3, "Carbon-Carbon σ-Bond Formation", Ed., G. Pattenden, Pergamon Press (1991); C. Bonini and G. Righi, Synthesis, 1994, 225.
10. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions of epoxides: K. Kudo, K. Saigo, Y. Hashimoto, K. Saito, and M. Hasegawa, Chem. Lett., 1992, 1449; K. Kudo, Y. Hashimoto, H. Houchigai, M. Hasegawa, and K. Saigo, Bull. Chem. Soc.jpn., 1993, 66, 848; K. Kudo, Y. Hashimoto, M. Sukegawa, M. Hasegawa, and K. Saigo, J.org. Chem., 1993, 58, 579; Y. Hashimoto, Y. Sato, N. Takeshita, K. Kudo, and K. Saigo, Tetrahedron, 1994, 50, 8317; H. Miyauchi, T. Nakamura, and N. Ohashi, Bull. Chem.soc. Jpn., 1995, 68, 1731; H. Miyauchi and N. Ohashi, Bull. Chem. Soc. Jpn., 1995, 68, 3591; C. Liu, K. Kudo, Y. Hashimoto, and K. Saigo, J. Org. Chem., 1996, 61, 494; C. Liu, Y. Hashimoto, K. Kudo, and K. Saigo, Bull. Chem. Soc. Jpn., 1996, 69, 2095; D. M. Gill, N.A. Pegg, and C. M. Rayner, Tetrahedron, 1996, 52, 3609.
11. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions ofepoxides: K. Kudo, K. Saigo, Y. Hashimoto, K. Saito, and M. Hasegawa, Chem. Lett., 1992, 1449; K. Kudo, Y. Hashimoto, H. Houchigai, M. Hasegawa, and K. Saigo, Bull. Chem. Soc. Jpn., 1993, 66, 848; K. Kudo, Y. Hashimoto, M. Sukegawa, M. Hasegawa, and K. Saigo, J.org. Chem., 1993, 58, 579; Y. Hashimoto, Y. Sato, N. Takeshita, K. Kudo, and K. Saigo, Tetrahedron, 1994, 50, 8317; H. Miyauchi, T. Nakamura, and N. Ohashi, Bull. Chem.soc. Jpn., 1995, 68, 1731; H. Miyauchi and N. Ohashi, Bull. Chem. Soc. Jpn., 1995, 68, 3591; C. Liu, K. Kudo, Y. Hashimoto, and K. Saigo, J. Org. Chem., 1996, 61, 494; C. Liu, Y. Hashimoto, K. Kudo, and K. Saigo, Bull. Chem. Soc. Jpn., 1996, 69, 2095; D. M. Gill, N.A. Pegg, and C. M. Rayner, Tetrahedron, 1996, 52, 3609.
12. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions ofepoxides: K. Kudo, K. Saigo, Y. Hashimoto, K. Saito, and M. Hasegawa, Chem. Lett., 1992, 1449; K. Kudo, Y. Hashimoto, H. Houchigai, M. Hasegawa, and K. Saigo, Bull. Chem. Soc.jpn., 1993, 66, 848; K. Kudo, Y. Hashimoto, M. Sukegawa, M. Hasegawa, and K. Saigo, J. Org. Chem., 1993, 58, 579; Y. Hashimoto, Y. Sato, N. Takeshita, K. Kudo, and K. Saigo, Tetrahedron, 1994, 50, 8317; H. Miyauchi, T. Nakamura, and N. Ohashi, Bull. Chem.soc. Jpn., 1995, 68, 1731; H. Miyauchi and N. Ohashi, Bull. Chem. Soc. Jpn., 1995, 68, 3591; C. Liu, K. Kudo, Y. Hashimoto, and K. Saigo, J. Org. Chem., 1996, 61, 494; C. Liu, Y. Hashimoto, K. Kudo, and K. Saigo, Bull. Chem. Soc. Jpn., 1996, 69, 2095; D. M. Gill, N.A. Pegg, and C. M. Rayner, Tetrahedron, 1996, 52, 3609.
13. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions ofepoxides: K. Kudo, K. Saigo, Y. Hashimoto, K. Saito, and M. Hasegawa, Chem. Lett., 1992, 1449; K. Kudo, Y. Hashimoto, H. Houchigai, M. Hasegawa, and K. Saigo, Bull. Chem. Soc.jpn., 1993, 66, 848; K. Kudo, Y. Hashimoto, M. Sukegawa, M. Hasegawa, and K. Saigo, J.org. Chem., 1993, 58, 579; Y. Hashimoto, Y. Sato, N. Takeshita, K. Kudo, and K. Saigo, Tetrahedron, 1994, 50, 8317; H. Miyauchi, T. Nakamura, and N. Ohashi, Bull. Chem.soc. Jpn., 1995, 68, 1731; H. Miyauchi and N. Ohashi, Bull. Chem. Soc. Jpn., 1995, 68, 3591; C. Liu, K. Kudo, Y. Hashimoto, and K. Saigo, J. Org. Chem., 1996, 61, 494; C. Liu, Y. Hashimoto, K. Kudo, and K. Saigo, Bull. Chem. Soc. Jpn., 1996, 69, 2095; D. M. Gill, N.A. Pegg, and C. M. Rayner, Tetrahedron, 1996, 52, 3609.
14. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions ofepoxides: K. Kudo, K. Saigo, Y. Hashimoto, K. Saito, and M. Hasegawa, Chem. Lett., 1992, 1449; K. Kudo, Y. Hashimoto, H. Houchigai, M. Hasegawa, and K. Saigo, Bull. Chem. Soc.jpn., 1993, 66, 848; K. Kudo, Y. Hashimoto, M. Sukegawa, M. Hasegawa, and K. Saigo, J.org. Chem., 1993, 58, 579; Y. Hashimoto, Y. Sato, N. Takeshita, K. Kudo, and K. Saigo, Tetrahedron, 1994, 50, 8317; H. Miyauchi, T. Nakamura, and N. Ohashi, Bull. Chem. Soc. Jpn., 1995, 68, 1731; H. Miyauchi and N. Ohashi, Bull. Chem. Soc. Jpn., 1995, 68, 3591; C. Liu, K. Kudo, Y. Hashimoto, and K. Saigo, J. Org. Chem., 1996, 61, 494; C. Liu, Y. Hashimoto, K. Kudo, and K. Saigo, Bull. Chem. Soc. Jpn., 1996, 69, 2095; D. M. Gill, N.A. Pegg, and C. M. Rayner, Tetrahedron, 1996, 52, 3609.
15. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions ofepoxides: K. Kudo, K. Saigo, Y. Hashimoto, K. Saito, and M. Hasegawa, Chem. Lett., 1992, 1449; K. Kudo, Y. Hashimoto, H. Houchigai, M. Hasegawa, and K. Saigo, Bull. Chem. Soc.jpn., 1993, 66, 848; K. Kudo, Y. Hashimoto, M. Sukegawa, M. Hasegawa, and K. Saigo, J.org. Chem., 1993, 58, 579; Y. Hashimoto, Y. Sato, N. Takeshita, K. Kudo, and K. Saigo, Tetrahedron, 1994, 50, 8317; H. Miyauchi, T. Nakamura, and N. Ohashi, Bull. Chem.soc. Jpn., 1995, 68, 1731; H. Miyauchi and N. Ohashi, Bull. Chem. Soc. Jpn., 1995, 68, 3591; C. Liu, K. Kudo, Y. Hashimoto, and K. Saigo, J. Org. Chem., 1996, 61, 494; C. Liu, Y. Hashimoto, K. Kudo, and K. Saigo, Bull. Chem. Soc. Jpn., 1996, 69, 2095; D. M. Gill, N.A. Pegg, and C. M. Rayner, Tetrahedron, 1996, 52, 3609.
16. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions ofepoxides: K. Kudo, K. Saigo, Y. Hashimoto, K. Saito, and M. Hasegawa, Chem. Lett., 1992, 1449; K. Kudo, Y. Hashimoto, H. Houchigai, M. Hasegawa, and K. Saigo, Bull. Chem. Soc.jpn., 1993, 66, 848; K. Kudo, Y. Hashimoto, M. Sukegawa, M. Hasegawa, and K. Saigo, J.org. Chem., 1993, 58, 579; Y. Hashimoto, Y. Sato, N. Takeshita, K. Kudo, and K. Saigo, Tetrahedron, 1994, 50, 8317; H. Miyauchi, T. Nakamura, and N. Ohashi, Bull. Chem.soc. Jpn., 1995, 68, 1731; H. Miyauchi and N. Ohashi, Bull. Chem. Soc. Jpn., 1995, 68, 3591; C. Liu, K. Kudo, Y. Hashimoto, and K. Saigo, J. Org. Chem., 1996, 61, 494; C. Liu, Y. Hashimoto, K. Kudo, and K. Saigo, Bull. Chem. Soc. Jpn., 1996, 69, 2095; D. M. Gill, N.A. Pegg, and C. M. Rayner, Tetrahedron, 1996, 52, 3609.
17. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions ofepoxides: K. Kudo, K. Saigo, Y. Hashimoto, K. Saito, and M. Hasegawa, Chem. Lett., 1992, 1449; K. Kudo, Y. Hashimoto, H. Houchigai, M. Hasegawa, and K. Saigo, Bull. Chem. Soc.jpn., 1993, 66, 848; K. Kudo, Y. Hashimoto, M. Sukegawa, M. Hasegawa, and K. Saigo, J.org. Chem., 1993, 58, 579; Y. Hashimoto, Y. Sato, N. Takeshita, K. Kudo, and K. Saigo, Tetrahedron, 1994, 50, 8317; H. Miyauchi, T. Nakamura, and N. Ohashi, Bull. Chem.soc. Jpn., 1995, 68, 1731; H. Miyauchi and N. Ohashi, Bull. Chem. Soc. Jpn., 1995, 68, 3591; C. Liu, K. Kudo, Y. Hashimoto, and K. Saigo, J. Org. Chem., 1996, 61, 494; C. Liu, Y. Hashimoto, K. Kudo, and K. Saigo, Bull. Chem. Soc. Jpn., 1996, 69, 2095; D. M. Gill, N.A. Pegg, and C. M. Rayner, Tetrahedron, 1996, 52, 3609.
18. Synthetic reactions via episulfonium ions and sulfur-directed ring-opening reactions ofepoxides: K. Kudo, K. Saigo, Y. Hashimoto, K. Saito, and M. Hasegawa, Chem. Lett., 1992, 1449; K. Kudo, Y. Hashimoto, H. Houchigai, M. Hasegawa, and K. Saigo, Bull. Chem. Soc.jpn., 1993, 66, 848; K. Kudo, Y. Hashimoto, M. Sukegawa, M. Hasegawa, and K. Saigo, J.org. Chem., 1993, 58, 579; Y. Hashimoto, Y. Sato, N. Takeshita, K. Kudo, and K. Saigo, Tetrahedron, 1994, 50, 8317; H. Miyauchi, T. Nakamura, and N. Ohashi, Bull. Chem.soc. Jpn., 1995, 68, 1731; H. Miyauchi and N. Ohashi, Bull. Chem. Soc. Jpn., 1995, 68, 3591; C. Liu, K. Kudo, Y. Hashimoto, and K. Saigo, J. Org. Chem., 1996, 61, 494; C. Liu, Y. Hashimoto, K. Kudo, and K. Saigo, Bull. Chem. Soc. Jpn., 1996, 69, 2095; D. M. Gill, N. A. Pegg, and C. M. Rayner, Tetrahedron, 1996, 52, 3609.
19. H. G. Peer, Rec. Trav., 1960, 79, 825; W. Nagata, K. Okada and T. Aoki, Synthesis, 1979, 365.
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21. Authentic samples can be readily prepared from the starting allylic alcohols by the three-step reaction sequence: 1) osmylation; 2) sulfenylation of the resulting triols with diphenyl disulfide; 3) boronation of 2,3-diols with phenylboronic acid in benzene, in good overall yields. (Equation Presented)
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