A highly enantioselective phase-transfer catalyzed epoxidation of enones with a mild oxidant, trichloroisocyanuric acid

Chemical Communications

Volumn , Issue 21, 2003, Pages 2714-2715

  Ye, Jinxing ^a   Wang, Yongcan ^a   Liu, Renhua ^a   Zhang, Guofu ^a   Zhang, Qing ^a   Chen, Jiping ^a   Liang, Xinmiao ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHALCONE DERIVATIVE; CYANURIC ACID; EPOXIDE; EPOXYKETONE; KETONE; OXIDIZING AGENT; QUATERNARY AMMONIUM DERIVATIVE; SYMCLOSENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; EPOXIDATION; PHASE TRANSITION;

EID: 0242693237     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b308042k     Document Type: Article

References (22)

1. R. A. Johnson and K. B. Sharpless, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, New York, Seoul, Tokyo, 1991, vol. 7, p. 389.
2. For a recent review on the asymmetric epoxidation of electron-deficient alkenes, see: M. J. Porter and J. Skidmore, Chem. Commun., 2000, 1215.
3. (a) B. Lygo and P. G. Wainwright, Tetrahedron Lett., 1998, 39, 1599;
4. (b) B. Lygo and P. G. Wainwright, Tetrahedron, 1999, 55, 6289;
5. (c) B. Lygo and D. C. M. To, Tetrahedron Lett., 2001, 42, 1343;
6. (d) B. Lygo and D. C. M. To, Chem. Commun., 2003, 2360.
7. (a) S. Arai, H. Tsuge and T. Shioiri, Tetrahedron Lett., 1998, 39, 7563;
8. (b) S. Arai, H. Tsuge, M. Oku, M. Miura and T. Shioiri, Tetrahedron, 2002, 58, 1623.
9. E. J. Corey and F.-Y. Zhang, Org. Lett., 1999, 1, 1287.
10. W. Adam, P. B. Rao, H-G. Degen, A. Levai, T. Patonay and C. R. Saha-Möller, J. Org. Chem., 2002, 67, 259.
11. For a recent review on use of trichloroisocyanuric acid, see: U. Tilstam and H. Weinmann, Org. Process Res. Dev., 2002, 4, 384. For selected examples on the use of trichloroisocyanuric acid see: (a) E. C. Juenge and D. A. Beal, Tetrahedron Lett., 1968, 55, 5819; (b) T. Cohen, Z. Kosarych, K. Suzuki and L.-C. Yu, J. Org. Chem., 1985, 50, 2965; (c) T. R. Walters, W. W. Jr. Zajac and J. M. Woods, J. Org. Chem., 1991, 56, 316; (d) G. A. Hiegel and M. Nalbandy, Synth. Commun., 1992, 22, 1589; (e) L. De Luca, G. Giacomelli and A. Porcheddu, Org. Lett., 2001, 3, 3041; (f) L. De Luca, G. Giacomelli, M. Simonetta and A. Porcheddu, J. Org. Chem., 2003, 68, 4999.
12. For a recent review on use of trichloroisocyanuric acid, see: U. Tilstam and H. Weinmann, Org. Process Res. Dev., 2002, 4, 384. For selected examples on the use of trichloroisocyanuric acid see: (a) E. C. Juenge and D. A. Beal, Tetrahedron Lett., 1968, 55, 5819; (b) T. Cohen, Z. Kosarych, K. Suzuki and L.-C. Yu, J. Org. Chem., 1985, 50, 2965; (c) T. R. Walters, W. W. Jr. Zajac and J. M. Woods, J. Org. Chem., 1991, 56, 316; (d) G. A. Hiegel and M. Nalbandy, Synth. Commun., 1992, 22, 1589; (e) L. De Luca, G. Giacomelli and A. Porcheddu, Org. Lett., 2001, 3, 3041; (f) L. De Luca, G. Giacomelli, M. Simonetta and A. Porcheddu, J. Org. Chem., 2003, 68, 4999.
13. For a recent review on use of trichloroisocyanuric acid, see: U. Tilstam and H. Weinmann, Org. Process Res. Dev., 2002, 4, 384. For selected examples on the use of trichloroisocyanuric acid see: (a) E. C. Juenge and D. A. Beal, Tetrahedron Lett., 1968, 55, 5819; (b) T. Cohen, Z. Kosarych, K. Suzuki and L.-C. Yu, J. Org. Chem., 1985, 50, 2965; (c) T. R. Walters, W. W. Jr. Zajac and J. M. Woods, J. Org. Chem., 1991, 56, 316; (d) G. A. Hiegel and M. Nalbandy, Synth. Commun., 1992, 22, 1589; (e) L. De Luca, G. Giacomelli and A. Porcheddu, Org. Lett., 2001, 3, 3041; (f) L. De Luca, G. Giacomelli, M. Simonetta and A. Porcheddu, J. Org. Chem., 2003, 68, 4999.
14. For a recent review on use of trichloroisocyanuric acid, see: U. Tilstam and H. Weinmann, Org. Process Res. Dev., 2002, 4, 384. For selected examples on the use of trichloroisocyanuric acid see: (a) E. C. Juenge and D. A. Beal, Tetrahedron Lett., 1968, 55, 5819; (b) T. Cohen, Z. Kosarych, K. Suzuki and L.-C. Yu, J. Org. Chem., 1985, 50, 2965; (c) T. R. Walters, W. W. Jr. Zajac and J. M. Woods, J. Org. Chem., 1991, 56, 316; (d) G. A. Hiegel and M. Nalbandy, Synth. Commun., 1992, 22, 1589; (e) L. De Luca, G. Giacomelli and A. Porcheddu, Org. Lett., 2001, 3, 3041; (f) L. De Luca, G. Giacomelli, M. Simonetta and A. Porcheddu, J. Org. Chem., 2003, 68, 4999.
15. For a recent review on use of trichloroisocyanuric acid, see: U. Tilstam and H. Weinmann, Org. Process Res. Dev., 2002, 4, 384. For selected examples on the use of trichloroisocyanuric acid see: (a) E. C. Juenge and D. A. Beal, Tetrahedron Lett., 1968, 55, 5819; (b) T. Cohen, Z. Kosarych, K. Suzuki and L.-C. Yu, J. Org. Chem., 1985, 50, 2965; (c) T. R. Walters, W. W. Jr. Zajac and J. M. Woods, J. Org. Chem., 1991, 56, 316; (d) G. A. Hiegel and M. Nalbandy, Synth. Commun., 1992, 22, 1589; (e) L. De Luca, G. Giacomelli and A. Porcheddu, Org. Lett., 2001, 3, 3041; (f) L. De Luca, G. Giacomelli, M. Simonetta and A. Porcheddu, J. Org. Chem., 2003, 68, 4999.
16. For a recent review on use of trichloroisocyanuric acid, see: U. Tilstam and H. Weinmann, Org. Process Res. Dev., 2002, 4, 384. For selected examples on the use of trichloroisocyanuric acid see: (a) E. C. Juenge and D. A. Beal, Tetrahedron Lett., 1968, 55, 5819; (b) T. Cohen, Z. Kosarych, K. Suzuki and L.-C. Yu, J. Org. Chem., 1985, 50, 2965; (c) T. R. Walters, W. W. Jr. Zajac and J. M. Woods, J. Org. Chem., 1991, 56, 316; (d) G. A. Hiegel and M. Nalbandy, Synth. Commun., 1992, 22, 1589; (e) L. De Luca, G. Giacomelli and A. Porcheddu, Org. Lett., 2001, 3, 3041; (f) L. De Luca, G. Giacomelli, M. Simonetta and A. Porcheddu, J. Org. Chem., 2003, 68, 4999.
17. For a recent review on use of trichloroisocyanuric acid, see: U. Tilstam and H. Weinmann, Org. Process Res. Dev., 2002, 4, 384. For selected examples on the use of trichloroisocyanuric acid see: (a) E. C. Juenge and D. A. Beal, Tetrahedron Lett., 1968, 55, 5819; (b) T. Cohen, Z. Kosarych, K. Suzuki and L.-C. Yu, J. Org. Chem., 1985, 50, 2965; (c) T. R. Walters, W. W. Jr. Zajac and J. M. Woods, J. Org. Chem., 1991, 56, 316; (d) G. A. Hiegel and M. Nalbandy, Synth. Commun., 1992, 22, 1589; (e) L. De Luca, G. Giacomelli and A. Porcheddu, Org. Lett., 2001, 3, 3041; (f) L. De Luca, G. Giacomelli, M. Simonetta and A. Porcheddu, J. Org. Chem., 2003, 68, 4999.
18. The preparation of racemic epoxides from alkenes by reaction with TCCA in aqueous acetone followed by treatment of the resulting chlorohydrin with aqueous KOH in ether/pentane, see: M. Wengert, A. M. Sanseverino and M. C. S. de Mattos, J. Braz. Chem. Soc., 2002, 13, 700.
19. (a) T. Schlama, L. Alcaraz and C. Mioskowski, Synlett, 1996, 571;
20. (b) W. S. Johnson, C. D. Gutsche and R. D. Offenhauer, J. Am. Chem. Soc., 1946, 68, 1648;
21. R. Levine and J. R. Stephens, J. Am. Chem. Soc., 1950, 72, 1642.
22. H.-g. Park, B.-s. Jeong, M.-S. Yoo, J.-H. Lee, M.-k. Park. Y.-J. Lee, M.-J. Kim and S.-s. Jew, Angew. Chem., Int. Ed., 2002, 41, 3036.