The C-2 selective azide opening reaction of trans-2,3-epoxy alcohols by NaN3 and PhB(OH)2

Tetrahedron Letters

Volumn 40, Issue 24, 1999, Pages 4589-4592

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

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AZIDE; BENZENEBORONIC ACID; BORONIC ACID DERIVATIVE; EPOXIDE; NITROGEN DERIVATIVE; SODIUM DERIVATIVE; SODIUM NITRATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033546108     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00798-4     Document Type: Article

References (22)

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; M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J. Chem. Soc. Chem. Commun., 1988, 1173; 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.
2. 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; M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J. Chem. Soc. Chem. Commun., 1988, 1173; 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.
3. 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; M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J. Chem. Soc. Chem. Commun., 1988, 1173; 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.
4. 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; M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J. Chem. Soc. Chem. Commun., 1988, 1173; 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.
5. 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; M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J. Chem. Soc. Chem. Commun., 1988, 1173; 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.
6. 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; M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J. Chem. Soc. Chem. Commun., 1988, 1173; 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.
7. 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; M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J. Chem. Soc. Chem. Commun., 1988, 1173; 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.
8. 2 M. Pastó, P. Castejón, A. Moyano, M. A. Pericàs, and A. Riera, J. Org. Chem., 1996, 61, 6033; F. Benedetti, S. Miertus, S. Norbedo, A. Tossi, and P. Zlatoidzky, J. Org. Chem.,1997, 62, 9348; J. Jurczak, "Preparative Carbohydrate Chemistry" S. Hannesian, Ed., NewYork, Marcel Dekker, 595 (1997).
9. 2 M. Pastó, P. Castejón, A. Moyano, M. A. Pericàs, and A. Riera, J. Org. Chem., 1996, 61,6033; F. Benedetti, S. Miertus, S. Norbedo, A. Tossi, and P. Zlatoidzky, J. Org. Chem., 1997, 62, 9348; J. Jurczak, "Preparative Carbohydrate Chemistry" S. Hannesian, Ed., NewYork, Marcel Dekker, 595 (1997).
10. 2 M. Pastó, P. Castejón, A. Moyano, M. A. Pericàs, and A. Riera, J. Org. Chem., 1996, 61,6033; F. Benedetti, S. Miertus, S. Norbedo, A. Tossi, and P. Zlatoidzky, J. Org. Chem.,1997, 62, 9348; J. Jurczak, "Preparative Carbohydrate Chemistry" S. Hannesian, Ed., New York, Marcel Dekker, 595 (1997).
11. 3 K. Maruoka, H. Sano, and H. Yamamoto, Chem. Lett., 1985, 599.
12. 4 C. H. Behrens and K. B. Sharpless, J. Org. Chem., 1985, 50, 5696.
13. 5 M. Onaka, K. Sugita, and Y. Izumi, Chem. Lett., 1986, 1327.
14. 6 M. Caron, P. R. Carlier, and K. B. Sharpless, J. Org. Chem., 1988, 53, 5185.
15. 7 S. Saito, S. Yamashita, T. Nishikawa, Y. Yokoyama, M. Inaba, and T. Moriwake, Tetrahedron Lett., 1989, 30, 4153.
16. 8 K. I. Sutowardoyo, M. Emziane, P. Lhoste, and D. Sinou, Tetrahedron, 1991, 47, 1435.
17. 9 F. Benedetti, F. Berti, and S. Norbedo, Tetrahedron Lett., 1998, 39, 7971.
18. 10 T. K. Chakraborty and G. V. Reddy, Tetrahedron Lett., 1991, 32, 679.
19. 11 The stereochemistry of two phenylboronates in entry 7 was confirmed by identification with that of authentic samples which were synthesized by phenylboronation of the corresponding 2-azido-1,3-diol and 3-azido-1,2-diol, respectively, readily prepared according to ref. 6.
20. 12 The boronates are hydrolyzed to the corresponding diols by treatment with pinacol or 1,3-propanediol in aqueous acetone.
21. 13 Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, and K. B. Sharpless, J. Am. Chem. Soc., 1987, 709, 5765; T. Katsuki and V. S. Martin, Org. React., 1996, 48, 1.
22. 13 Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, and K. B. Sharpless, J. Am.Chem. Soc., 1987, 709, 5765; T. Katsuki and V. S. Martin, Org. React., 1996, 48, 1.