Hydrophobic polymer-supported catalyst for organic reactions in water: Acid-catalyzed hydrolysis of thioesters and transprotection of thiols

Organic Letters

Volumn 5, Issue 2, 2003, Pages 101-103

  Iimura, Shinya ^a   Manabe, Kei ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

POLYESTER; SULFONIC ACID DERIVATIVE; THIOESTER; THIOL DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; HYDROLYSIS; HYDROPHOBICITY; POLYMERIZATION;

EID: 0037644458     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026906m     Document Type: Article

References (39)

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8. For recent examples of polymer-supported catalysts that work in water, see: (a) Nagayama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 2000, 39, 567. (b) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843. (c) Bergbreiter, D. E.; Case, B. L.; Liu, Y.-S.; Caraway, J. W. Macromolecules 1998, 31, 6053. (d) Chen, C.-W.; Chen, M.-Q.; Serizawa, T.; Akashi, M. Chem. Commun. 1998, 831. (e) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (f) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (g) Sakamoto, T.; Pac, C. J. Tetrahedron Lett. 2000, 41, 10009. (h) Yamada, Y. M. A.; Ichinohe, M.; Takahashi, H.; Ikegami, S. Org. Lett. 2001, 3, 1837. (i) Masaki, Y.; Yamada, T.; Tanaka, N. Synlett 2001, 1311.
9. For recent examples of polymer-supported catalysts that work in water, see: (a) Nagayama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 2000, 39, 567. (b) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843. (c) Bergbreiter, D. E.; Case, B. L.; Liu, Y.-S.; Caraway, J. W. Macromolecules 1998, 31, 6053. (d) Chen, C.-W.; Chen, M.-Q.; Serizawa, T.; Akashi, M. Chem. Commun. 1998, 831. (e) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (f) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (g) Sakamoto, T.; Pac, C. J. Tetrahedron Lett. 2000, 41, 10009. (h) Yamada, Y. M. A.; Ichinohe, M.; Takahashi, H.; Ikegami, S. Org. Lett. 2001, 3, 1837. (i) Masaki, Y.; Yamada, T.; Tanaka, N. Synlett 2001, 1311.
10. For recent examples of polymer-supported catalysts that work in water, see: (a) Nagayama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 2000, 39, 567. (b) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843. (c) Bergbreiter, D. E.; Case, B. L.; Liu, Y.-S.; Caraway, J. W. Macromolecules 1998, 31, 6053. (d) Chen, C.-W.; Chen, M.-Q.; Serizawa, T.; Akashi, M. Chem. Commun. 1998, 831. (e) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (f) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (g) Sakamoto, T.; Pac, C. J. Tetrahedron Lett. 2000, 41, 10009. (h) Yamada, Y. M. A.; Ichinohe, M.; Takahashi, H.; Ikegami, S. Org. Lett. 2001, 3, 1837. (i) Masaki, Y.; Yamada, T.; Tanaka, N. Synlett 2001, 1311.
11. For recent examples of polymer-supported catalysts that work in water, see: (a) Nagayama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 2000, 39, 567. (b) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843. (c) Bergbreiter, D. E.; Case, B. L.; Liu, Y.-S.; Caraway, J. W. Macromolecules 1998, 31, 6053. (d) Chen, C.-W.; Chen, M.-Q.; Serizawa, T.; Akashi, M. Chem. Commun. 1998, 831. (e) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (f) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (g) Sakamoto, T.; Pac, C. J. Tetrahedron Lett. 2000, 41, 10009. (h) Yamada, Y. M. A.; Ichinohe, M.; Takahashi, H.; Ikegami, S. Org. Lett. 2001, 3, 1837. (i) Masaki, Y.; Yamada, T.; Tanaka, N. Synlett 2001, 1311.
12. For recent examples of polymer-supported catalysts that work in water, see: (a) Nagayama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 2000, 39, 567. (b) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843. (c) Bergbreiter, D. E.; Case, B. L.; Liu, Y.-S.; Caraway, J. W. Macromolecules 1998, 31, 6053. (d) Chen, C.-W.; Chen, M.-Q.; Serizawa, T.; Akashi, M. Chem. Commun. 1998, 831. (e) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (f) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (g) Sakamoto, T.; Pac, C. J. Tetrahedron Lett. 2000, 41, 10009. (h) Yamada, Y. M. A.; Ichinohe, M.; Takahashi, H.; Ikegami, S. Org. Lett. 2001, 3, 1837. (i) Masaki, Y.; Yamada, T.; Tanaka, N. Synlett 2001, 1311.
13. For recent examples of polymer-supported catalysts that work in water, see: (a) Nagayama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 2000, 39, 567. (b) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843. (c) Bergbreiter, D. E.; Case, B. L.; Liu, Y.-S.; Caraway, J. W. Macromolecules 1998, 31, 6053. (d) Chen, C.-W.; Chen, M.-Q.; Serizawa, T.; Akashi, M. Chem. Commun. 1998, 831. (e) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (f) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (g) Sakamoto, T.; Pac, C. J. Tetrahedron Lett. 2000, 41, 10009. (h) Yamada, Y. M. A.; Ichinohe, M.; Takahashi, H.; Ikegami, S. Org. Lett. 2001, 3, 1837. (i) Masaki, Y.; Yamada, T.; Tanaka, N. Synlett 2001, 1311.
14. For recent examples of polymer-supported catalysts that work in water, see: (a) Nagayama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 2000, 39, 567. (b) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843. (c) Bergbreiter, D. E.; Case, B. L.; Liu, Y.-S.; Caraway, J. W. Macromolecules 1998, 31, 6053. (d) Chen, C.-W.; Chen, M.-Q.; Serizawa, T.; Akashi, M. Chem. Commun. 1998, 831. (e) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (f) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (g) Sakamoto, T.; Pac, C. J. Tetrahedron Lett. 2000, 41, 10009. (h) Yamada, Y. M. A.; Ichinohe, M.; Takahashi, H.; Ikegami, S. Org. Lett. 2001, 3, 1837. (i) Masaki, Y.; Yamada, T.; Tanaka, N. Synlett 2001, 1311.
15. For recent examples of polymer-supported catalysts that work in water, see: (a) Nagayama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 2000, 39, 567. (b) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843. (c) Bergbreiter, D. E.; Case, B. L.; Liu, Y.-S.; Caraway, J. W. Macromolecules 1998, 31, 6053. (d) Chen, C.-W.; Chen, M.-Q.; Serizawa, T.; Akashi, M. Chem. Commun. 1998, 831. (e) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (f) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (g) Sakamoto, T.; Pac, C. J. Tetrahedron Lett. 2000, 41, 10009. (h) Yamada, Y. M. A.; Ichinohe, M.; Takahashi, H.; Ikegami, S. Org. Lett. 2001, 3, 1837. (i) Masaki, Y.; Yamada, T.; Tanaka, N. Synlett 2001, 1311.
16. Polymer-supported sulfonic acid catalyzed hydrolysis of oxoesters has been reported; see: (a) Thomas, G. G.; Davies, C. W. Nature 1947, 159, 372. (b) Haskell, V. C.; Hammett, L. P. J. Am. Chem. Soc. 1949, 71, 1284. (c) Sakurada, I.; Sakaguchi, Y.; Ono, T.; Ueda, T. Makromol. Chem. 1966, 91, 243. (d) Yoshikawa, S.; Kim, O.-K. Bull. Chem. Soc. Jpn. 1966, 39, 1515. Quite recently, we reported use of polymer-supported sulfonic acids for oxoester formation in water: (e) Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2002, 344, 270.
17. Polymer-supported sulfonic acid catalyzed hydrolysis of oxoesters has been reported; see: (a) Thomas, G. G.; Davies, C. W. Nature 1947, 159, 372. (b) Haskell, V. C.; Hammett, L. P. J. Am. Chem. Soc. 1949, 71, 1284. (c) Sakurada, I.; Sakaguchi, Y.; Ono, T.; Ueda, T. Makromol. Chem. 1966, 91, 243. (d) Yoshikawa, S.; Kim, O.-K. Bull. Chem. Soc. Jpn. 1966, 39, 1515. Quite recently, we reported use of polymer-supported sulfonic acids for oxoester formation in water: (e) Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2002, 344, 270.
18. Polymer-supported sulfonic acid catalyzed hydrolysis of oxoesters has been reported; see: (a) Thomas, G. G.; Davies, C. W. Nature 1947, 159, 372. (b) Haskell, V. C.; Hammett, L. P. J. Am. Chem. Soc. 1949, 71, 1284. (c) Sakurada, I.; Sakaguchi, Y.; Ono, T.; Ueda, T. Makromol. Chem. 1966, 91, 243. (d) Yoshikawa, S.; Kim, O.-K. Bull. Chem. Soc. Jpn. 1966, 39, 1515. Quite recently, we reported use of polymer-supported sulfonic acids for oxoester formation in water: (e) Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2002, 344, 270.
19. Polymer-supported sulfonic acid catalyzed hydrolysis of oxoesters has been reported; see: (a) Thomas, G. G.; Davies, C. W. Nature 1947, 159, 372. (b) Haskell, V. C.; Hammett, L. P. J. Am. Chem. Soc. 1949, 71, 1284. (c) Sakurada, I.; Sakaguchi, Y.; Ono, T.; Ueda, T. Makromol. Chem. 1966, 91, 243. (d) Yoshikawa, S.; Kim, O.-K. Bull. Chem. Soc. Jpn. 1966, 39, 1515. Quite recently, we reported use of polymer-supported sulfonic acids for oxoester formation in water: (e) Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2002, 344, 270.
20. Polymer-supported sulfonic acid catalyzed hydrolysis of oxoesters has been reported; see: (a) Thomas, G. G.; Davies, C. W. Nature 1947, 159, 372. (b) Haskell, V. C.; Hammett, L. P. J. Am. Chem. Soc. 1949, 71, 1284. (c) Sakurada, I.; Sakaguchi, Y.; Ono, T.; Ueda, T. Makromol. Chem. 1966, 91, 243. (d) Yoshikawa, S.; Kim, O.-K. Bull. Chem. Soc. Jpn. 1966, 39, 1515. Quite recently, we reported use of polymer-supported sulfonic acids for oxoester formation in water: (e) Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2002, 344, 270.
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33. 3H (0.755 mmol/g) gave 10% yield under the conditions shown in Table 1.
34. The sulfonic acid content was estimated as 0.930 mmol/g from acid-base titration.
35. 2O/THF (rt, 72 h) gave 95% yield (Me ester, 46% ee), 97% yield (33% ee), 89% yield (27% ee), and 81% yield (36% ee), respectively.
36. 3H hardly proceeded in water.
37. For a recent example of organic reactions using odorless thiols, see: Node, M.; Kumar, K.; Nishide, K.; Ohsugi, S.; Miyamoto, T. Tetrahedron Lett. 2001, 42, 9207.
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