Phase-transfer-catalyzed asymmetric Darzens reaction

Tetrahedron

Volumn 55, Issue 20, 1999, Pages 6375-6386

  Arai, Shigeru ^a   Shirai, Yoshiki ^a   Ishida, Toshimasa ^b   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b OSAKA MEDICAL COLLEGE   (Japan)

Author keywords

Asymmetric catalyst; Darzens reactions; Epoxides; Phase transfer

Indexed keywords

CINCHONINE; KETONE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; ENANTIOMER; PHASE TRANSITION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0033553382     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00213-6     Document Type: Article

References (26)

1. 1. (a) Ohkata, K.; Kimura, J.; Shinohara, Y.; Takagi, R.; Hiraga, Y. Chem. Commun. 1996, 2411-2412. (b) Takahashi, T.; Muraoka, M.; Capo, M.; Koga, K. Chem. Pharm. Bull. 1995, 43, 1821-1823.
2. 1. (a) Ohkata, K.; Kimura, J.; Shinohara, Y.; Takagi, R.; Hiraga, Y. Chem. Commun. 1996, 2411-2412. (b) Takahashi, T.; Muraoka, M.; Capo, M.; Koga, K. Chem. Pharm. Bull. 1995, 43, 1821-1823.
3. 2. For recent books on PTC, see: (a) Phase-Transfer Catalysis. Mechanism and Syntheses; Halpern, M. E., Ed.; American Chemical Society, Washington D C, 1997. (b) Handbook of Phase Transfer Catalysis; Sasson, Y; Neumann, R. Ed.; Blackie A. & M., London, 1997.
4. 2. For recent books on PTC, see: (a) Phase-Transfer Catalysis. Mechanism and Syntheses; Halpern, M.E., Ed.; American Chemical Society, Washington D C, 1997. (b) Handbook of Phase Transfer Catalysis; Sasson, Y; Neumann, R. Ed.; Blackie A. & M., London, 1997.
5. 3. Preliminary reports of this and related works have appeared, see: (a) Arai, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2145-2148. (b) Arai, S.; Shirai, Y.; Ishida, T.; Shioiri, T. Chem. Commun. 1999, 49-50. See also (c) Arai, S.; Ishida, T.; Shioiri, T. Tetrahedron Lett. 1998, 39, 8299-8302.
6. 3. Preliminary reports of this and related works have appeared, see: (a) Arai, S.; Shioiri, T. TetrahedronLett. 1998, 39, 2145-2148. (b) Arai, S.; Shirai, Y.; Ishida, T.; Shioiri, T. Chem. Commun. 1999, 49-50. See also (c) Arai, S.; Ishida, T.; Shioiri, T. Tetrahedron Lett. 1998, 39, 8299-8302.
7. 3. Preliminary reports of this and related works have appeared, see: (a) Arai, S.; Shioiri, T. TetrahedronLett. 1998, 39, 2145-2148. (b) Arai, S.; Shirai, Y.; Ishida, T.; Shioiri, T. Chem. Commun. 1999, 49-50. See also (c) Arai, S.; Ishida, T.; Shioiri, T. Tetrahedron Lett. 1998, 39, 8299-8302.
8. 4. Quite recently, we have reported the successful asymmetric reactions promoted by chiral PTC, see (a) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997-3000. (b) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563-7566. (c) Arai, S.; Oku, M.; Miura, M.; Shioiri, T.Synlett 1998, 1201-1202. (d) Arai, S.; Nakayama, K. Hatano, K.; Shioiri, T. J. Org. Chem. 1998, 63, 9572-9575. (e) Arai, S.; Nakayama, K.; Suzuki, Y.; Hatano, K.; Shioiri, T. Tetrahedron Lett.1998, 39, 9739-9742.
9. 4. Quite recently, we have reported the successful asymmetric reactions promoted by chiral PTC, see (a)Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997-3000. (b) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563-7566. (c) Arai, S.; Oku, M.; Miura, M.; Shioiri, T.Synlett 1998, 1201-1202. (d) Arai, S.; Nakayama, K. Hatano, K.; Shioiri, T. J. Org. Chem. 1998, 63, 9572-9575. (e) Arai, S.; Nakayama, K.; Suzuki, Y.; Hatano, K.; Shioiri, T. Tetrahedron Lett.1998, 39, 9739-9742.
10. 4. Quite recently, we have reported the successful asymmetric reactions promoted by chiral PTC, see (a)Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997-3000. (b) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563-7566. (c) Arai, S.; Oku, M.; Miura, M.; Shioiri, T. Synlett 1998, 1201-1202. (d) Arai, S.; Nakayama, K. Hatano, K.; Shioiri, T. J. Org. Chem. 1998, 63, 9572-9575. (e) Arai, S.; Nakayama, K.; Suzuki, Y.; Hatano, K.; Shioiri, T. Tetrahedron Lett.1998, 39, 9739-9742.
11. 4. Quite recently, we have reported the successful asymmetric reactions promoted by chiral PTC, see (a)Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997-3000. (b) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563-7566. (c) Arai, S.; Oku, M.; Miura, M.; Shioiri, T.Synlett 1998, 1201-1202. (d) Arai, S.; Nakayama, K. Hatano, K.; Shioiri, T. J. Org. Chem. 1998, 63, 9572-9575. (e) Arai, S.; Nakayama, K.; Suzuki, Y.; Hatano, K.; Shioiri, T. Tetrahedron Lett.1998, 39, 9739-9742.
12. 4. Quite recently, we have reported the successful asymmetric reactions promoted by chiral PTC, see (a)Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997-3000. (b) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563-7566. (c) Arai, S.; Oku, M.; Miura, M.; Shioiri, T.Synlett 1998, 1201-1202. (d) Arai, S.; Nakayama, K. Hatano, K.; Shioiri, T. J. Org. Chem. 1998, 63, 9572-9575. (e) Arai, S.; Nakayama, K.; Suzuki, Y.; Hatano, K.; Shioiri, T. Tetrahedron Lett. 1998, 39, 9739-9742.
13. 5. PTC A was purchased from Aldrich, Co. Ltd.
14. 6. Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc., 1997, 119, 2329-2330. (b) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murry, P. J. Angew. Chem.Int. Ed. Engl. 1997, 36, 410-412.
15. 6. Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc., 1997, 119, 2329-2330. (b) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murry, P. J. Angew. Chem. Int. Ed. Engl. 1997, 36, 410-412.
16. 7. Recently, the chiral crown ether catalyzed asymmetric Darzens reaction was reported, see: Bako, P.; Szollosy, A.; Bombicz, P.; Toke, L. Synlett, 1997, 291-292.
17. 8. Unpublished results.
18. 9. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
19. 10. Molander, G. A. Chem. Rev. 1992, 92, 29-68, and references cited therein.
20. 11. Hojo, M.; Harada, H.; Itoh, H.; Hosomi, A. J. Am. Chem. Soc. 1997, 119, 5459-5460.
21. 12. O'Donnell and co-workers reported experiments leading to the proposal of the O-alkylated salt as an active catalyst in alkylation reaction: O'Donnell, M. J.; Wu, S.; Huffmann, J. C. Tetrahedron 1994, 50, 4507-4518.
22. 13. Quite recently, successful examples of the asymmetric reactions promoted by the O-allyl-cinchonine or cinchonidine derived PTCs have been reported, see (a) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347-5350. (b) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (c) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1998, 39, 1599-1602. (d)O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778.
23. 13. Quite recently, successful examples of the asymmetric reactions promoted by the O-allyl-cinchonine orcinchonidine derived PTCs have been reported, see (a) Corey, E. J.; Noe, M. C.; Xu, F. TetrahedronLett. 1998, 39, 5347-5350. (b) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (c) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1998, 39, 1599-1602. (d)O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778.
24. 13. Quite recently, successful examples of the asymmetric reactions promoted by the O-allyl-cinchonine orcinchonidine derived PTCs have been reported, see (a) Corey, E. J.; Noe, M. C.; Xu, F. TetrahedronLett. 1998, 39, 5347-5350. (b) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (c) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1998, 39, 1599-1602. (d)O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778.
25. 13. Quite recently, successful examples of the asymmetric reactions promoted by the O-allyl-cinchonine orcinchonidine derived PTCs have been reported, see (a) Corey, E. J.; Noe, M. C.; Xu, F. TetrahedronLett. 1998, 39, 5347-5350. (b) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (c) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1998, 39, 1599-1602. (d) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778.
26. 14. Mukaiyama,T.; Haga, T.; Iwasawa, N.; Chem. Lett. 1982, 1601-1604. No transformation to epoxide or epimerization of α-hydrogen occurred by use of the corresponding syn adduct 8b as a starting material under similar conditions.