Highly stereoselective Lewis acid mediated conjugate radical additions to methyl α-D-glucopyranoside derivatives tethering an unsaturated ester moiety at C-4

Synlett

Volumn , Issue 7, 2000, Pages 979-982

  Munakata, Ryosuke ^a   Totani, Kiichiro ^a   Takao, Ken Ichi ^a   Tadano, Kin Ichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Carbohydrates; Conjugate additions; Radical reactions

Indexed keywords

GLYCOPYRANOSIDE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; STEREOCHEMISTRY;

EID: 0033931575     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (36)

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5. For leading reviews on asymmetric 1,4-conjugate addition, see the following: Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771. Noyori, R. Asymmetric Catalysts in Organic Synthesis; John Wiley and Sons: New York, 1994. Alexakis, A. In Orgaocopper Reagents, A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, U.K., 1994; p. 159. Feringa, B. L.; deVries, A. H. M. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press Inc: Greenwich, CT; 1995; Vol. 1, p 151.
6. For leading reviews on asymmetric 1,4-conjugate addition, see the following: Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771. Noyori, R. Asymmetric Catalysts in Organic Synthesis; John Wiley and Sons: New York, 1994. Alexakis, A. In Orgaocopper Reagents, A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, U.K., 1994; p. 159. Feringa, B. L.; deVries, A. H. M. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press Inc: Greenwich, CT; 1995; Vol. 1, p 151.
7. For leading reviews on asymmetric 1,4-conjugate addition, see the following: Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771. Noyori, R. Asymmetric Catalysts in Organic Synthesis; John Wiley and Sons: New York, 1994. Alexakis, A. In Orgaocopper Reagents, A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, U.K., 1994; p. 159. Feringa, B. L.; deVries, A. H. M. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press Inc: Greenwich, CT; 1995; Vol. 1, p 151.
8. For recent reports on this subject, see the following: Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779. Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 9200. Sibi. M. P.; Ji J. J. Org. Chem. 1997, 62, 3800. Iserloh, U.; Curran, D. P.; Kanemasa, S. Tetrahedron: Asymmetry 1999, 10, 2417. Sibi, M. P.; Ji, J.; Sausker, J. B.; Jasperse, C. P. J. Am. Chem. Soc. 1999, 121, 751.
9. For recent reports on this subject, see the following: Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779. Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 9200. Sibi. M. P.; Ji J. J. Org. Chem. 1997, 62, 3800. Iserloh, U.; Curran, D. P.; Kanemasa, S. Tetrahedron: Asymmetry 1999, 10, 2417. Sibi, M. P.; Ji, J.; Sausker, J. B.; Jasperse, C. P. J. Am. Chem. Soc. 1999, 121, 751.
10. For recent reports on this subject, see the following: Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779. Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 9200. Sibi. M. P.; Ji J. J. Org. Chem. 1997, 62, 3800. Iserloh, U.; Curran, D. P.; Kanemasa, S. Tetrahedron: Asymmetry 1999, 10, 2417. Sibi, M. P.; Ji, J.; Sausker, J. B.; Jasperse, C. P. J. Am. Chem. Soc. 1999, 121, 751.
11. For recent reports on this subject, see the following: Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779. Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 9200. Sibi. M. P.; Ji J. J. Org. Chem. 1997, 62, 3800. Iserloh, U.; Curran, D. P.; Kanemasa, S. Tetrahedron: Asymmetry 1999, 10, 2417. Sibi, M. P.; Ji, J.; Sausker, J. B.; Jasperse, C. P. J. Am. Chem. Soc. 1999, 121, 751.
12. For recent reports on this subject, see the following: Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779. Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 9200. Sibi. M. P.; Ji J. J. Org. Chem. 1997, 62, 3800. Iserloh, U.; Curran, D. P.; Kanemasa, S. Tetrahedron: Asymmetry 1999, 10, 2417. Sibi, M. P.; Ji, J.; Sausker, J. B.; Jasperse, C. P. J. Am. Chem. Soc. 1999, 121, 751.
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14. Stang, P. J. Acc. Chem. Res. 1991, 24, 304. Smadja, W. Synlett 1994, 1. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996. Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562.
15. Stang, P. J. Acc. Chem. Res. 1991, 24, 304. Smadja, W. Synlett 1994, 1. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996. Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562.
16. Stang, P. J. Acc. Chem. Res. 1991, 24, 304. Smadja, W. Synlett 1994, 1. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996. Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562.
17. For other works utilizing carbohydrate-based templates, see the following: Cintas, P. Tetrahedron 1991, 47, 6079. Kunz, H.; Rück, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 336. Kunz, H. Pure Appl. Chem. 1995, 67, 1627. Hultin, P. G.; Earle, M. A.; Sudharshan, M. Tetrahedron 1997, 53, 14823.
18. For other works utilizing carbohydrate-based templates, see the following: Cintas, P. Tetrahedron 1991, 47, 6079. Kunz, H.; Rück, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 336. Kunz, H. Pure Appl. Chem. 1995, 67, 1627. Hultin, P. G.; Earle, M. A.; Sudharshan, M. Tetrahedron 1997, 53, 14823.
19. For other works utilizing carbohydrate-based templates, see the following: Cintas, P. Tetrahedron 1991, 47, 6079. Kunz, H.; Rück, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 336. Kunz, H. Pure Appl. Chem. 1995, 67, 1627. Hultin, P. G.; Earle, M. A.; Sudharshan, M. Tetrahedron 1997, 53, 14823.
20. For other works utilizing carbohydrate-based templates, see the following: Cintas, P. Tetrahedron 1991, 47, 6079. Kunz, H.; Rück, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 336. Kunz, H. Pure Appl. Chem. 1995, 67, 1627. Hultin, P. G.; Earle, M. A.; Sudharshan, M. Tetrahedron 1997, 53, 14823.
21. Totani, K.; Nagatsuka, T.; Takao, K.; Tadano, K. Org. Lett. 1999, 1, 1447.
22. Compounds 1b and 1d were prepared in the conventional manner from methyl 4,6-O-benzylidene-α-D-glucopyranoside; protection of 2, 3-OH followed by debenzylidenation, iodination of 6-OH via the respective tosylate, hydrogenolysis and then esterification of 4-OH with crotonic anhydride.
23. Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143. Oshima, K.; Utimoto, K. J. Synth. Org. Chem. Jpn. 1989, 47, 40.
24. Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143. Oshima, K.; Utimoto, K. J. Synth. Org. Chem. Jpn. 1989, 47, 40.
25. Giese, B. Angew. Chem., Int. Ed. Engl. 1985, 24, 553. Neumann, W. P. Synthesis 1987, 665. Curran. D. P. Synthesis 1988, 417.
26. Giese, B. Angew. Chem., Int. Ed. Engl. 1985, 24, 553. Neumann, W. P. Synthesis 1987, 665. Curran. D. P. Synthesis 1988, 417.
27. Giese, B. Angew. Chem., Int. Ed. Engl. 1985, 24, 553. Neumann, W. P. Synthesis 1987, 665. Curran. D. P. Synthesis 1988, 417.
28. Nozaki, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 2585. Shibata, I.; Baba, A. J. Synth. Org. Chem. Jpn. 1998, 56, 280.
29. Nozaki, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 2585. Shibata, I.; Baba, A. J. Synth. Org. Chem. Jpn. 1998, 56, 280.
30. Giacomelli, G.; Lardicci, L.; Caporusso, A. M. J. Chem. Soc., Perkin Trans. I 1975, 1795.
31. No other organoaluminum compounds were examined as the Lewis acid.
32. 13C NMR, IR, and HRMS.
33. The ratio and stereochemistry of each adduct were assigned based on comparison of the retention times with those of authentic 4R and 4S derived from the mixture of 2aR and 2aS, whose stereochemistry had been determined.
34. 1H NMR.
35. 7S (3-methylpentanoic acid): Wiberg, K. B.; Rowland, B. I. J. Am. Chem. Soc. 1955, 77, 1159. (3,4,4-trimethylpentanoic acid): Azzena, U.; Luisi, P. L.; Suter, U. W. Gladiali, S. Helv. Chim. Acta 1981, 64, 2821.
36. 7S (3-methylpentanoic acid): Wiberg, K. B.; Rowland, B. I. J. Am. Chem. Soc. 1955, 77, 1159. (3,4,4-trimethylpentanoic acid): Azzena, U.; Luisi, P. L.; Suter, U. W. Gladiali, S. Helv. Chim. Acta 1981, 64, 2821.