Inositol synthesis: Concise preparation of L-chiro-inositol and muco- inositol from a common intermediate

Tetrahedron Asymmetry

Volumn 9, Issue 12, 1998, Pages 2011-2014

  Brammer Jr , Larry E ^a   Hudlicky, Tomas ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE; INOSITOL;

ARTICLE; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0344352491     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00182-7     Document Type: Article

References (46)

1. (a) Inositol Phosphates and Derivatives: Synthesis, Biochemistry, and Therapeutic Potential; Reitz, A. B., Ed., American Chemical Society: Washington, 1991;
2. (b) Berridge, M. J.; Irvine, R. F. Nature 1989, 341, 197;
3. (c) Cosgrove, D. J. In Inositol Phosphates: Their Chemistry, Biochemistry, and Physiology; Elsevier: Amsterdam, 1980;
4. (d) Wells, W. W.; Eisenbrg, F. In Cyclitols and Phosphoinositides I; Academic Press: New York, 1978.
5. Hudlicky, T.; Price, J. D.; Rulin, F.; Tsunoda, T. J. Am. Chem. Soc. 1990, 112, 9439.
6. (a) Gibson, D. T.; Hensley, M.; Yoshioka, H.; Mabry, T. J. Biochemistry 1970, 9, 1626;
7. (b) Gibson, D. T.; Koch, G. R.; Kallio, R. E. Biochemistry 1968, 7, 2653.
8. Mandel, M.; Hudlicky, T.; Kwart, K. D.; Whited, G. M. J. Org. Chem. 1993, 55, 2331.
9. (a) Mandel, M.; Hudlicky, T. J. Chem. Soc., Perkin Trans. 1 1993, 741; corrigendum: Mandel, M.; Hudlicky, T. J. Chem. Soc., Perkin Trans. 1 1993, 1537.
10. (a) Mandel, M.; Hudlicky, T. J. Chem. Soc., Perkin Trans. 1 1993, 741; corrigendum: Mandel, M.; Hudlicky, T. J. Chem. Soc., Perkin Trans. 1 1993, 1537.
11. Hudlicky, T.; Mandel, M.; Rouden, J.; Lee, R. S.; Bachman, B.; Dudding, T.; Yost, K. J.; Merola, J. S. J. Chem. Soc., Perkin Trans. 1 1994, 1553.
12. Hudlicky, T.; Luna, H.; Olivo, H. F.; Andersen, C.; Nugent, T.; Price, J. D. J. Chem. Soc., Perkin Trans. 1 1991, 2907.
13. Hudlicky, T.; Olivo, H. F. Tetrahedron Lett. 1991, 32, 6077.
14. Hudlicky, T.; Olivo, H. F.; McKibben, B. J. Am. Chem. Soc. 1994, 116, 5108.
15. For comprehensive reviews of arene cis-diol chemistry see: (a) Prestwich, G. D. Acc. Chem. Res. 1996, 29, 503; (b) Reddy, K. K.; Rizo, J.; Falck, J. R. Tetrahedron Lett. 1997, 38, 4729; Cobb, J. E.; Johnson, M. R. Tetrahedron 1991, 47, 21; Roemer, S.; Stadler, C.; Rudolf, M. T.; Jastorff, B.; Schultz, C. J. Chem. Soc., Perkin Trans. 1 1993, 741; (e) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed., JAI Press: Greenwich, CT, 1993; Vol. 2, pp. 113-176; (f) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3; (g) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795; (h) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed., JAI Press: Greenwich, CT, 1995; p. 271; Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T.; Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC, 1996; Chapter 14; (j) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993; (k) Hudlicky, T. Chem. Rev. 1996, 96, 3; Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195; Grund, A. D. SIM News 1995, 45, 59; (n) Sheldrake, G. N. In Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992, Chapter 6, pp. 128-165.
16. For comprehensive reviews of arene cis-diol chemistry see: (a) Prestwich, G. D. Acc. Chem. Res. 1996, 29, 503; (b) Reddy, K. K.; Rizo, J.; Falck, J. R. Tetrahedron Lett. 1997, 38, 4729; Cobb, J. E.; Johnson, M. R. Tetrahedron 1991, 47, 21; Roemer, S.; Stadler, C.; Rudolf, M. T.; Jastorff, B.; Schultz, C. J. Chem. Soc., Perkin Trans. 1 1993, 741; (e) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed., JAI Press: Greenwich, CT, 1993; Vol. 2, pp. 113-176; (f) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3; (g) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795; (h) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed., JAI Press: Greenwich, CT, 1995; p. 271; Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T.; Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC, 1996; Chapter 14; (j) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993; (k) Hudlicky, T. Chem. Rev. 1996, 96, 3; Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195; Grund, A. D. SIM News 1995, 45, 59; (n) Sheldrake, G. N. In Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992, Chapter 6, pp. 128-165.
17. For comprehensive reviews of arene cis-diol chemistry see: (a) Prestwich, G. D. Acc. Chem. Res. 1996, 29, 503; (b) Reddy, K. K.; Rizo, J.; Falck, J. R. Tetrahedron Lett. 1997, 38, 4729; Cobb, J. E.; Johnson, M. R. Tetrahedron 1991, 47, 21; Roemer, S.; Stadler, C.; Rudolf, M. T.; Jastorff, B.; Schultz, C. J. Chem. Soc., Perkin Trans. 1 1993, 741; (e) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed., JAI Press: Greenwich, CT, 1993; Vol. 2, pp. 113-176; (f) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3; (g) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795; (h) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed., JAI Press: Greenwich, CT, 1995; p. 271; Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T.; Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC, 1996; Chapter 14; (j) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993; (k) Hudlicky, T. Chem. Rev. 1996, 96, 3; Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195; Grund, A. D. SIM News 1995, 45, 59; (n) Sheldrake, G. N. In Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992, Chapter 6, pp. 128-165.
18. For comprehensive reviews of arene cis-diol chemistry see: (a) Prestwich, G. D. Acc. Chem. Res. 1996, 29, 503; (b) Reddy, K. K.; Rizo, J.; Falck, J. R. Tetrahedron Lett. 1997, 38, 4729; Cobb, J. E.; Johnson, M. R. Tetrahedron 1991, 47, 21; Roemer, S.; Stadler, C.; Rudolf, M. T.; Jastorff, B.; Schultz, C. J. Chem. Soc., Perkin Trans. 1 1993, 741; (e) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed., JAI Press: Greenwich, CT, 1993; Vol. 2, pp. 113-176; (f) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3; (g) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795; (h) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed., JAI Press: Greenwich, CT, 1995; p. 271; Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T.; Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC, 1996; Chapter 14; (j) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993; (k) Hudlicky, T. Chem. Rev. 1996, 96, 3; Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195; Grund, A. D. SIM News 1995, 45, 59; (n) Sheldrake, G. N. In Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992, Chapter 6, pp. 128-165.
19. For comprehensive reviews of arene cis-diol chemistry see: (a) Prestwich, G. D. Acc. Chem. Res. 1996, 29, 503; (b) Reddy, K. K.; Rizo, J.; Falck, J. R. Tetrahedron Lett. 1997, 38, 4729; Cobb, J. E.; Johnson, M. R. Tetrahedron 1991, 47, 21; Roemer, S.; Stadler, C.; Rudolf, M. T.; Jastorff, B.; Schultz, C. J. Chem. Soc., Perkin Trans. 1 1993, 741; (e) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed., JAI Press: Greenwich, CT, 1993; Vol. 2, pp. 113-176; (f) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3; (g) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795; (h) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed., JAI Press: Greenwich, CT, 1995; p. 271; Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T.; Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC, 1996; Chapter 14; (j) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993; (k) Hudlicky, T. Chem. Rev. 1996, 96, 3; Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195; Grund, A. D. SIM News 1995, 45, 59; (n) Sheldrake, G. N. In Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992, Chapter 6, pp. 128-165.
20. For comprehensive reviews of arene cis-diol chemistry see: (a) Prestwich, G. D. Acc. Chem. Res. 1996, 29, 503; (b) Reddy, K. K.; Rizo, J.; Falck, J. R. Tetrahedron Lett. 1997, 38, 4729; Cobb, J. E.; Johnson, M. R. Tetrahedron 1991, 47, 21; Roemer, S.; Stadler, C.; Rudolf, M. T.; Jastorff, B.; Schultz, C. J. Chem. Soc., Perkin Trans. 1 1993, 741; (e) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed., JAI Press: Greenwich, CT, 1993; Vol. 2, pp. 113-176; (f) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3; (g) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795; (h) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed., JAI Press: Greenwich, CT, 1995; p. 271; Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T.; Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC, 1996; Chapter 14; (j) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993; (k) Hudlicky, T. Chem. Rev. 1996, 96, 3; Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195; Grund, A. D. SIM News 1995, 45, 59; (n) Sheldrake, G. N. In Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992, Chapter 6, pp. 128-165.
21. For comprehensive reviews of arene cis-diol chemistry see: (a) Prestwich, G. D. Acc. Chem. Res. 1996, 29, 503; (b) Reddy, K. K.; Rizo, J.; Falck, J. R. Tetrahedron Lett. 1997, 38, 4729; Cobb, J. E.; Johnson, M. R. Tetrahedron 1991, 47, 21; Roemer, S.; Stadler, C.; Rudolf, M. T.; Jastorff, B.; Schultz, C. J. Chem. Soc., Perkin Trans. 1 1993, 741; (e) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed., JAI Press: Greenwich, CT, 1993; Vol. 2, pp. 113-176; (f) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3; (g) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795; (h) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed., JAI Press: Greenwich, CT, 1995; p. 271; Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T.; Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC, 1996; Chapter 14; (j) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993; (k) Hudlicky, T. Chem. Rev. 1996, 96, 3; Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195; Grund, A. D. SIM News 1995, 45, 59; (n) Sheldrake, G. N. In Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992, Chapter 6, pp. 128-165.
22. For comprehensive reviews of arene cis-diol chemistry see: (a) Prestwich, G. D. Acc. Chem. Res. 1996, 29, 503; (b) Reddy, K. K.; Rizo, J.; Falck, J. R. Tetrahedron Lett. 1997, 38, 4729; Cobb, J. E.; Johnson, M. R. Tetrahedron 1991, 47, 21; Roemer, S.; Stadler, C.; Rudolf, M. T.; Jastorff, B.; Schultz, C. J. Chem. Soc., Perkin Trans. 1 1993, 741; (e) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed., JAI Press: Greenwich, CT, 1993; Vol. 2, pp. 113-176; (f) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3; (g) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795; (h) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed., JAI Press: Greenwich, CT, 1995; p. 271; Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T.; Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC, 1996; Chapter 14; (j) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993; (k) Hudlicky, T. Chem. Rev. 1996, 96, 3; Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195; Grund, A. D. SIM News 1995, 45, 59; (n) Sheldrake, G. N. In Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992, Chapter 6, pp. 128-165.
23. For comprehensive reviews of arene cis-diol chemistry see: (a) Prestwich, G. D. Acc. Chem. Res. 1996, 29, 503; (b) Reddy, K. K.; Rizo, J.; Falck, J. R. Tetrahedron Lett. 1997, 38, 4729; Cobb, J. E.; Johnson, M. R. Tetrahedron 1991, 47, 21; Roemer, S.; Stadler, C.; Rudolf, M. T.; Jastorff, B.; Schultz, C. J. Chem. Soc., Perkin Trans. 1 1993, 741; (e) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed., JAI Press: Greenwich, CT, 1993; Vol. 2, pp. 113-176; (f) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3; (g) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795; (h) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed., JAI Press: Greenwich, CT, 1995; p. 271; Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T.; Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC, 1996; Chapter 14; (j) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993; (k) Hudlicky, T. Chem. Rev. 1996, 96, 3; Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195; Grund, A. D. SIM News 1995, 45, 59; (n) Sheldrake, G. N. In Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992, Chapter 6, pp. 128-165.
24. For comprehensive reviews of arene cis-diol chemistry see: (a) Prestwich, G. D. Acc. Chem. Res. 1996, 29, 503; (b) Reddy, K. K.; Rizo, J.; Falck, J. R. Tetrahedron Lett. 1997, 38, 4729; Cobb, J. E.; Johnson, M. R. Tetrahedron 1991, 47, 21; Roemer, S.; Stadler, C.; Rudolf, M. T.; Jastorff, B.; Schultz, C. J. Chem. Soc., Perkin Trans. 1 1993, 741; (e) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed., JAI Press: Greenwich, CT, 1993; Vol. 2, pp. 113-176; (f) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3; (g) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795; (h) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed., JAI Press: Greenwich, CT, 1995; p. 271; Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T.; Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC, 1996; Chapter 14; (j) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993; (k) Hudlicky, T. Chem. Rev. 1996, 96, 3; Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195; Grund, A. D. SIM News 1995, 45, 59; (n) Sheldrake, G. N. In Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992, Chapter 6, pp. 128-165.
25. For comprehensive reviews of arene cis-diol chemistry see: (a) Prestwich, G. D. Acc. Chem. Res. 1996, 29, 503; (b) Reddy, K. K.; Rizo, J.; Falck, J. R. Tetrahedron Lett. 1997, 38, 4729; Cobb, J. E.; Johnson, M. R. Tetrahedron 1991, 47, 21; Roemer, S.; Stadler, C.; Rudolf, M. T.; Jastorff, B.; Schultz, C. J. Chem. Soc., Perkin Trans. 1 1993, 741; (e) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed., JAI Press: Greenwich, CT, 1993; Vol. 2, pp. 113-176; (f) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3; (g) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795; (h) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed., JAI Press: Greenwich, CT, 1995; p. 271; Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T.; Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC, 1996; Chapter 14; (j) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993; (k) Hudlicky, T. Chem. Rev. 1996, 96, 3; Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195; Grund, A. D. SIM News 1995, 45, 59; (n) Sheldrake, G. N. In Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992, Chapter 6, pp. 128-165.
26. For comprehensive reviews of arene cis-diol chemistry see: (a) Prestwich, G. D. Acc. Chem. Res. 1996, 29, 503; (b) Reddy, K. K.; Rizo, J.; Falck, J. R. Tetrahedron Lett. 1997, 38, 4729; Cobb, J. E.; Johnson, M. R. Tetrahedron 1991, 47, 21; Roemer, S.; Stadler, C.; Rudolf, M. T.; Jastorff, B.; Schultz, C. J. Chem. Soc., Perkin Trans. 1 1993, 741; (e) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed., JAI Press: Greenwich, CT, 1993; Vol. 2, pp. 113-176; (f) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3; (g) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795; (h) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed., JAI Press: Greenwich, CT, 1995; p. 271; Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T.; Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC, 1996; Chapter 14; (j) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993; (k) Hudlicky, T. Chem. Rev. 1996, 96, 3; Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195; Grund, A. D. SIM News 1995, 45, 59; (n) Sheldrake, G. N. In Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992, Chapter 6, pp. 128-165.
27. For comprehensive reviews of arene cis-diol chemistry see: (a) Prestwich, G. D. Acc. Chem. Res. 1996, 29, 503; (b) Reddy, K. K.; Rizo, J.; Falck, J. R. Tetrahedron Lett. 1997, 38, 4729; Cobb, J. E.; Johnson, M. R. Tetrahedron 1991, 47, 21; Roemer, S.; Stadler, C.; Rudolf, M. T.; Jastorff, B.; Schultz, C. J. Chem. Soc., Perkin Trans. 1 1993, 741; (e) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed., JAI Press: Greenwich, CT, 1993; Vol. 2, pp. 113-176; (f) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3; (g) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795; (h) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed., JAI Press: Greenwich, CT, 1995; p. 271; Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T.; Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC, 1996; Chapter 14; (j) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993; (k) Hudlicky, T. Chem. Rev. 1996, 96, 3; Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195; Grund, A. D. SIM News 1995, 45, 59; (n) Sheldrake, G. N. In Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992, Chapter 6, pp. 128-165.
28. For comprehensive reviews of arene cis-diol chemistry see: (a) Prestwich, G. D. Acc. Chem. Res. 1996, 29, 503; (b) Reddy, K. K.; Rizo, J.; Falck, J. R. Tetrahedron Lett. 1997, 38, 4729; Cobb, J. E.; Johnson, M. R. Tetrahedron 1991, 47, 21; Roemer, S.; Stadler, C.; Rudolf, M. T.; Jastorff, B.; Schultz, C. J. Chem. Soc., Perkin Trans. 1 1993, 741; (e) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed., JAI Press: Greenwich, CT, 1993; Vol. 2, pp. 113-176; (f) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3; (g) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795; (h) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed., JAI Press: Greenwich, CT, 1995; p. 271; Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T.; Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC, 1996; Chapter 14; (j) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993; (k) Hudlicky, T. Chem. Rev. 1996, 96, 3; Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195; Grund, A. D. SIM News 1995, 45, 59; (n) Sheldrake, G. N. In Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1992, Chapter 6, pp. 128-165.
29. For previous syntheses see: (a) Kornienko, A.; d'Alarcao, M. Tetrahedron Lett. 1997, 38, 6497 (asymmetric synthesis from D-xylose); (b) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895 (asymmetric synthesis from D-sorbitol); (c) Carless, H. A. J.; Busia, K.; Oak, O. Z. Synlett 1993, 672 (racemic); (d) Angyal, S. J.; MacDonald, C. G. J. Chem. Soc. 1952, 686 (asymmetric synthesis from quebrachitol).
30. For previous syntheses see: (a) Kornienko, A.; d'Alarcao, M. Tetrahedron Lett. 1997, 38, 6497 (asymmetric synthesis from D-xylose); (b) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895 (asymmetric synthesis from D-sorbitol); (c) Carless, H. A. J.; Busia, K.; Oak, O. Z. Synlett 1993, 672 (racemic); (d) Angyal, S. J.; MacDonald, C. G. J. Chem. Soc. 1952, 686 (asymmetric synthesis from quebrachitol).
31. For previous syntheses see: (a) Kornienko, A.; d'Alarcao, M. Tetrahedron Lett. 1997, 38, 6497 (asymmetric synthesis from D-xylose); (b) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895 (asymmetric synthesis from D-sorbitol); (c) Carless, H. A. J.; Busia, K.; Oak, O. Z. Synlett 1993, 672 (racemic); (d) Angyal, S. J.; MacDonald, C. G. J. Chem. Soc. 1952, 686 (asymmetric synthesis from quebrachitol).
32. For previous syntheses see: (a) Kornienko, A.; d'Alarcao, M. Tetrahedron Lett. 1997, 38, 6497 (asymmetric synthesis from D-xylose); (b) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895 (asymmetric synthesis from D-sorbitol); (c) Carless, H. A. J.; Busia, K.; Oak, O. Z. Synlett 1993, 672 (racemic); (d) Angyal, S. J.; MacDonald, C. G. J. Chem. Soc. 1952, 686 (asymmetric synthesis from quebrachitol).
33. For previous syntheses see: (a) Nakajima, M.; Tomida, I.; Kurihara, N.; Takai, S. Chem. Ber. 1959, 92, 173; (b) Angyal, S. J.; Bender, V.; Curtin, J. H. J. Chem. Soc. 1966, 798; (c) Dangschat, G; Fisher, H. O. L. Carbohyd. Res. 1987, 164, 343; (d) Carless, H. A. J.; Busia, K.; Oak, O. Z. Synlett 1993, 672 (racemic).
34. For previous syntheses see: (a) Nakajima, M.; Tomida, I.; Kurihara, N.; Takai, S. Chem. Ber. 1959, 92, 173; (b) Angyal, S. J.; Bender, V.; Curtin, J. H. J. Chem. Soc. 1966, 798; (c) Dangschat, G; Fisher, H. O. L. Carbohyd. Res. 1987, 164, 343; (d) Carless, H. A. J.; Busia, K.; Oak, O. Z. Synlett 1993, 672 (racemic).
35. For previous syntheses see: (a) Nakajima, M.; Tomida, I.; Kurihara, N.; Takai, S. Chem. Ber. 1959, 92, 173; (b) Angyal, S. J.; Bender, V.; Curtin, J. H. J. Chem. Soc. 1966, 798; (c) Dangschat, G; Fisher, H. O. L. Carbohyd. Res. 1987, 164, 343; (d) Carless, H. A. J.; Busia, K.; Oak, O. Z. Synlett 1993, 672 (racemic).
36. For previous syntheses see: (a) Nakajima, M.; Tomida, I.; Kurihara, N.; Takai, S. Chem. Ber. 1959, 92, 173; (b) Angyal, S. J.; Bender, V.; Curtin, J. H. J. Chem. Soc. 1966, 798; (c) Dangschat, G; Fisher, H. O. L. Carbohyd. Res. 1987, 164, 343; (d) Carless, H. A. J.; Busia, K.; Oak, O. Z. Synlett 1993, 672 (racemic).
37. Zylstra, G. J.; Gibson, D. T. J. Biol. Chem. 1989, 264, 14940.
38. Hudlicky, T.; Tian, X.; Konigsberger, K.; Rouden, J. J. Org. Chem. 1994, 59, 4037.
39. Chini, M.; Crotti, P.; Flippin, L. A.; Gardelli, C.; Giovani, E.; Macchia, F.; Pineschi, M. J. Org. Chem. 1993, 55, 1221.
40. (a) Tian, X.; Hudlicky, T.; Konigsberger, K. J. Am. Chem. Soc. 1995, 117, 3643;
41. (b) Hudlicky, T.; Tian, X.; Konigsberger, K.; Maurya, R.; Rouden, J.; Boreas, F. J. Am. Chem. Soc. 1996, 118, 10752;
42. (c) Tian, X.; Maurya, R.; Konigsberger, K.; Hudlicky, T. Synlett 1995, 1125.
43. For definition of this term see Ref. 10(k), p. 10.
44. Deslongschamps, P. In Stereos elective Effects in Organic Chemistry; Pergamon Press: Oxford, 1983.
45. Unpublished results from this laboratory.
46. Desjardins, M.; Brammer Jr., L. E.; Hudlicky, T. Carbohyd. Res. 1997, 340, 39.