Selective inversion of the proximal or distal hydroxyl groups in syn,syn-3-[N-(alkoxycarbonyl)ammo] 1,2-diols via cyclic sulfates

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 7162-7167

  Kemp, Scott J ^a   Bao, Jianming ^a   Pedersen, Steven F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001105276     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961060j     Document Type: Article

References (62)

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22. For some previous syntheses see: (a) Sugiyama, S.; Honda, M.; Higuchi, R.; Komori, T. Liebigs Ann. Chem. 1991, 349. (b) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Paola, P. J. Org. Chem. 1990, 55, 1439. (c) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1989, 30, 5507. (d) Kulmacz, R. J.; Schroepfer, G. J., Jr. J. Am. Chem. Soc. 1978, 100, 3963. (e) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1988, 619. (f) Mulzer, J.; Brand, C. Tetrahedron 1986, 42, 5961. (g) Schwab, W.; Jager, V. Angew. Chem., Int. Ed. Engl. 1981, 20, 603. (h) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1872. (i) Gigg, J.; Gigg, R. J. Chem. Soc. C 1966, 1876. (j) Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1879. (k) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1882. (l) Prostenik, M.; Majhofer-Orescanin, B.; Ries-Lesic, B.; Stanacev, N. Z. Tetrahedron 1965, 21, 651.
23. For some previous syntheses see: (a) Sugiyama, S.; Honda, M.; Higuchi, R.; Komori, T. Liebigs Ann. Chem. 1991, 349. (b) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Paola, P. J. Org. Chem. 1990, 55, 1439. (c) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1989, 30, 5507. (d) Kulmacz, R. J.; Schroepfer, G. J., Jr. J. Am. Chem. Soc. 1978, 100, 3963. (e) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1988, 619. (f) Mulzer, J.; Brand, C. Tetrahedron 1986, 42, 5961. (g) Schwab, W.; Jager, V. Angew. Chem., Int. Ed. Engl. 1981, 20, 603. (h) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1872. (i) Gigg, J.; Gigg, R. J. Chem. Soc. C 1966, 1876. (j) Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1879. (k) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1882. (l) Prostenik, M.; Majhofer-Orescanin, B.; Ries-Lesic, B.; Stanacev, N. Z. Tetrahedron 1965, 21, 651.
24. For some previous syntheses see: (a) Sugiyama, S.; Honda, M.; Higuchi, R.; Komori, T. Liebigs Ann. Chem. 1991, 349. (b) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Paola, P. J. Org. Chem. 1990, 55, 1439. (c) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1989, 30, 5507. (d) Kulmacz, R. J.; Schroepfer, G. J., Jr. J. Am. Chem. Soc. 1978, 100, 3963. (e) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1988, 619. (f) Mulzer, J.; Brand, C. Tetrahedron 1986, 42, 5961. (g) Schwab, W.; Jager, V. Angew. Chem., Int. Ed. Engl. 1981, 20, 603. (h) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1872. (i) Gigg, J.; Gigg, R. J. Chem. Soc. C 1966, 1876. (j) Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1879. (k) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1882. (l) Prostenik, M.; Majhofer-Orescanin, B.; Ries-Lesic, B.; Stanacev, N. Z. Tetrahedron 1965, 21, 651.
25. For some previous syntheses see: (a) Sugiyama, S.; Honda, M.; Higuchi, R.; Komori, T. Liebigs Ann. Chem. 1991, 349. (b) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Paola, P. J. Org. Chem. 1990, 55, 1439. (c) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1989, 30, 5507. (d) Kulmacz, R. J.; Schroepfer, G. J., Jr. J. Am. Chem. Soc. 1978, 100, 3963. (e) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1988, 619. (f) Mulzer, J.; Brand, C. Tetrahedron 1986, 42, 5961. (g) Schwab, W.; Jager, V. Angew. Chem., Int. Ed. Engl. 1981, 20, 603. (h) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1872. (i) Gigg, J.; Gigg, R. J. Chem. Soc. C 1966, 1876. (j) Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1879. (k) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1882. (l) Prostenik, M.; Majhofer-Orescanin, B.; Ries-Lesic, B.; Stanacev, N. Z. Tetrahedron 1965, 21, 651.
26. For some previous syntheses see: (a) Sugiyama, S.; Honda, M.; Higuchi, R.; Komori, T. Liebigs Ann. Chem. 1991, 349. (b) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Paola, P. J. Org. Chem. 1990, 55, 1439. (c) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1989, 30, 5507. (d) Kulmacz, R. J.; Schroepfer, G. J., Jr. J. Am. Chem. Soc. 1978, 100, 3963. (e) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1988, 619. (f) Mulzer, J.; Brand, C. Tetrahedron 1986, 42, 5961. (g) Schwab, W.; Jager, V. Angew. Chem., Int. Ed. Engl. 1981, 20, 603. (h) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1872. (i) Gigg, J.; Gigg, R. J. Chem. Soc. C 1966, 1876. (j) Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1879. (k) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1882. (l) Prostenik, M.; Majhofer-Orescanin, B.; Ries-Lesic, B.; Stanacev, N. Z. Tetrahedron 1965, 21, 651.
27. For some previous syntheses see: (a) Sugiyama, S.; Honda, M.; Higuchi, R.; Komori, T. Liebigs Ann. Chem. 1991, 349. (b) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Paola, P. J. Org. Chem. 1990, 55, 1439. (c) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1989, 30, 5507. (d) Kulmacz, R. J.; Schroepfer, G. J., Jr. J. Am. Chem. Soc. 1978, 100, 3963. (e) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1988, 619. (f) Mulzer, J.; Brand, C. Tetrahedron 1986, 42, 5961. (g) Schwab, W.; Jager, V. Angew. Chem., Int. Ed. Engl. 1981, 20, 603. (h) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1872. (i) Gigg, J.; Gigg, R. J. Chem. Soc. C 1966, 1876. (j) Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1879. (k) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1882. (l) Prostenik, M.; Majhofer-Orescanin, B.; Ries-Lesic, B.; Stanacev, N. Z. Tetrahedron 1965, 21, 651.
28. For some previous syntheses see: (a) Sugiyama, S.; Honda, M.; Higuchi, R.; Komori, T. Liebigs Ann. Chem. 1991, 349. (b) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Paola, P. J. Org. Chem. 1990, 55, 1439. (c) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1989, 30, 5507. (d) Kulmacz, R. J.; Schroepfer, G. J., Jr. J. Am. Chem. Soc. 1978, 100, 3963. (e) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1988, 619. (f) Mulzer, J.; Brand, C. Tetrahedron 1986, 42, 5961. (g) Schwab, W.; Jager, V. Angew. Chem., Int. Ed. Engl. 1981, 20, 603. (h) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1872. (i) Gigg, J.; Gigg, R. J. Chem. Soc. C 1966, 1876. (j) Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1879. (k) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1882. (l) Prostenik, M.; Majhofer-Orescanin, B.; Ries-Lesic, B.; Stanacev, N. Z. Tetrahedron 1965, 21, 651.
29. For some previous syntheses see: (a) Sugiyama, S.; Honda, M.; Higuchi, R.; Komori, T. Liebigs Ann. Chem. 1991, 349. (b) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Paola, P. J. Org. Chem. 1990, 55, 1439. (c) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1989, 30, 5507. (d) Kulmacz, R. J.; Schroepfer, G. J., Jr. J. Am. Chem. Soc. 1978, 100, 3963. (e) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1988, 619. (f) Mulzer, J.; Brand, C. Tetrahedron 1986, 42, 5961. (g) Schwab, W.; Jager, V. Angew. Chem., Int. Ed. Engl. 1981, 20, 603. (h) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1872. (i) Gigg, J.; Gigg, R. J. Chem. Soc. C 1966, 1876. (j) Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1879. (k) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1882. (l) Prostenik, M.; Majhofer-Orescanin, B.; Ries-Lesic, B.; Stanacev, N. Z. Tetrahedron 1965, 21, 651.
30. For some previous syntheses see: (a) Sugiyama, S.; Honda, M.; Higuchi, R.; Komori, T. Liebigs Ann. Chem. 1991, 349. (b) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Paola, P. J. Org. Chem. 1990, 55, 1439. (c) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1989, 30, 5507. (d) Kulmacz, R. J.; Schroepfer, G. J., Jr. J. Am. Chem. Soc. 1978, 100, 3963. (e) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1988, 619. (f) Mulzer, J.; Brand, C. Tetrahedron 1986, 42, 5961. (g) Schwab, W.; Jager, V. Angew. Chem., Int. Ed. Engl. 1981, 20, 603. (h) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1872. (i) Gigg, J.; Gigg, R. J. Chem. Soc. C 1966, 1876. (j) Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1879. (k) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1882. (l) Prostenik, M.; Majhofer-Orescanin, B.; Ries-Lesic, B.; Stanacev, N. Z. Tetrahedron 1965, 21, 651.
31. For some previous syntheses see: (a) Sugiyama, S.; Honda, M.; Higuchi, R.; Komori, T. Liebigs Ann. Chem. 1991, 349. (b) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Paola, P. J. Org. Chem. 1990, 55, 1439. (c) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1989, 30, 5507. (d) Kulmacz, R. J.; Schroepfer, G. J., Jr. J. Am. Chem. Soc. 1978, 100, 3963. (e) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1988, 619. (f) Mulzer, J.; Brand, C. Tetrahedron 1986, 42, 5961. (g) Schwab, W.; Jager, V. Angew. Chem., Int. Ed. Engl. 1981, 20, 603. (h) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1872. (i) Gigg, J.; Gigg, R. J. Chem. Soc. C 1966, 1876. (j) Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1879. (k) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1882. (l) Prostenik, M.; Majhofer-Orescanin, B.; Ries-Lesic, B.; Stanacev, N. Z. Tetrahedron 1965, 21, 651.
32. For some previous syntheses see: (a) Sugiyama, S.; Honda, M.; Higuchi, R.; Komori, T. Liebigs Ann. Chem. 1991, 349. (b) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Paola, P. J. Org. Chem. 1990, 55, 1439. (c) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1989, 30, 5507. (d) Kulmacz, R. J.; Schroepfer, G. J., Jr. J. Am. Chem. Soc. 1978, 100, 3963. (e) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1988, 619. (f) Mulzer, J.; Brand, C. Tetrahedron 1986, 42, 5961. (g) Schwab, W.; Jager, V. Angew. Chem., Int. Ed. Engl. 1981, 20, 603. (h) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1872. (i) Gigg, J.; Gigg, R. J. Chem. Soc. C 1966, 1876. (j) Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1879. (k) Gigg, J.; Gigg, R.; Warren, C. D. J. Chem. Soc. C 1966, 1882. (l) Prostenik, M.; Majhofer-Orescanin, B.; Ries-Lesic, B.; Stanacev, N. Z. Tetrahedron 1965, 21, 651.
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