Palladium-catalyzed enantiospecific reaction of propargylic carbonates with phenols: Cascade chirality transfer

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3325-3327

  Yoshida, Masahiro ^a   Fujita, Mika ^a   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONIC ACID DERIVATIVE; PALLADIUM; PHENOL DERIVATIVE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; REACTION ANALYSIS;

EID: 0141632683     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0351753     Document Type: Article

References (27)

1. For reviews on palladium-catalyzed reactions of propargylic compounds, see: (a) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (b) Minami, I.; Yuhara, M.; Watanabe, H.; Tsuji, J. J. Organomet. Chem. 1987, 334, 225. (c) Tsuji, J.; Mandai. T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589.
2. For reviews on palladium-catalyzed reactions of propargylic compounds, see: (a) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (b) Minami, I.; Yuhara, M.; Watanabe, H.; Tsuji, J. J. Organomet. Chem. 1987, 334, 225. (c) Tsuji, J.; Mandai. T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589.
3. For reviews on palladium-catalyzed reactions of propargylic compounds, see: (a) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (b) Minami, I.; Yuhara, M.; Watanabe, H.; Tsuji, J. J. Organomet. Chem. 1987, 334, 225. (c) Tsuji, J.; Mandai. T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589.
4. Tsuji, J.; Watanabe, H.; Minami, I.; Shimizu, I. J. Am. Chem. Soc. 1985, 107, 2196.
5. For recent examples of similar types of palladium-catalyzed reactions of propargylic carbonates with nucleophiles, see: (a) Fournier-Nguefack, C.; Lhoste, P.; Sinou, D. Synlett 1996, 553. (b) Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583. (c) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1999, 40, 9025. (d) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Org. Lett. 2000, 2, 527. (e) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (f) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (g) Damez, C.; Labrosse, J.-R.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 2003, 44, 557.
6. For recent examples of similar types of palladium-catalyzed reactions of propargylic carbonates with nucleophiles, see: (a) Fournier-Nguefack, C.; Lhoste, P.; Sinou, D. Synlett 1996, 553. (b) Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583. (c) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1999, 40, 9025. (d) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Org. Lett. 2000, 2, 527. (e) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (f) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (g) Damez, C.; Labrosse, J.-R.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 2003, 44, 557.
7. For recent examples of similar types of palladium-catalyzed reactions of propargylic carbonates with nucleophiles, see: (a) Fournier-Nguefack, C.; Lhoste, P.; Sinou, D. Synlett 1996, 553. (b) Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583. (c) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1999, 40, 9025. (d) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Org. Lett. 2000, 2, 527. (e) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (f) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (g) Damez, C.; Labrosse, J.-R.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 2003, 44, 557.
8. For recent examples of similar types of palladium-catalyzed reactions of propargylic carbonates with nucleophiles, see: (a) Fournier-Nguefack, C.; Lhoste, P.; Sinou, D. Synlett 1996, 553. (b) Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583. (c) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1999, 40, 9025. (d) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Org. Lett. 2000, 2, 527. (e) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (f) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (g) Damez, C.; Labrosse, J.-R.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 2003, 44, 557.
9. For recent examples of similar types of palladium-catalyzed reactions of propargylic carbonates with nucleophiles, see: (a) Fournier-Nguefack, C.; Lhoste, P.; Sinou, D. Synlett 1996, 553. (b) Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583. (c) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1999, 40, 9025. (d) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Org. Lett. 2000, 2, 527. (e) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (f) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (g) Damez, C.; Labrosse, J.-R.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 2003, 44, 557.
10. For recent examples of similar types of palladium-catalyzed reactions of propargylic carbonates with nucleophiles, see: (a) Fournier-Nguefack, C.; Lhoste, P.; Sinou, D. Synlett 1996, 553. (b) Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583. (c) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1999, 40, 9025. (d) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Org. Lett. 2000, 2, 527. (e) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (f) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (g) Damez, C.; Labrosse, J.-R.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 2003, 44, 557.
11. For recent examples of similar types of palladium-catalyzed reactions of propargylic carbonates with nucleophiles, see: (a) Fournier-Nguefack, C.; Lhoste, P.; Sinou, D. Synlett 1996, 553. (b) Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583. (c) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1999, 40, 9025. (d) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Org. Lett. 2000, 2, 527. (e) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (f) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (g) Damez, C.; Labrosse, J.-R.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 2003, 44, 557.
12. For reviews on stereochemical studies of palladium-catalyzed reactions of allylic compounds, see: (a) Tsuji, J. Tetrahedron 1986, 42, 4361. (b) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (c) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (d) Heumann, A.; Réglier, M. Tetrahedron 1995, 51, 975. (e) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
13. For reviews on stereochemical studies of palladium-catalyzed reactions of allylic compounds, see: (a) Tsuji, J. Tetrahedron 1986, 42, 4361. (b) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (c) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (d) Heumann, A.; Réglier, M. Tetrahedron 1995, 51, 975. (e) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
14. For reviews on stereochemical studies of palladium-catalyzed reactions of allylic compounds, see: (a) Tsuji, J. Tetrahedron 1986, 42, 4361. (b) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (c) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (d) Heumann, A.; Réglier, M. Tetrahedron 1995, 51, 975. (e) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
15. For reviews on stereochemical studies of palladium-catalyzed reactions of allylic compounds, see: (a) Tsuji, J. Tetrahedron 1986, 42, 4361. (b) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (c) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (d) Heumann, A.; Réglier, M. Tetrahedron 1995, 51, 975. (e) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
16. For reviews on stereochemical studies of palladium-catalyzed reactions of allylic compounds, see: (a) Tsuji, J. Tetrahedron 1986, 42, 4361. (b) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (c) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (d) Heumann, A.; Réglier, M. Tetrahedron 1995, 51, 975. (e) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
17. N2′ attack of palladium catalyst; see: (a) Elsevier: C. J.; Stehouwer, P. M.; Westmijze, H.; Vermeer, P. J. Org. Chem. 1983, 48, 1103. (b) Marshall, J. A.; Adams, N. D. J. Org. Chem. 1997, 62, 367. (c) Dixneuf, P.; Guyot, T.; Ness, M. D.; Roberts, S. M. Chem. Commun, 1997, 2083. (d) Konno, T.; Tanikawa, M.; Ishihara, T.; Yamanaka, H. Chem. Lett. 2000, 1360.
18. N2′ attack of palladium catalyst; see: (a) Elsevier: C. J.; Stehouwer, P. M.; Westmijze, H.; Vermeer, P. J. Org. Chem. 1983, 48, 1103. (b) Marshall, J. A.; Adams, N. D. J. Org. Chem. 1997, 62, 367. (c) Dixneuf, P.; Guyot, T.; Ness, M. D.; Roberts, S. M. Chem. Commun, 1997, 2083. (d) Konno, T.; Tanikawa, M.; Ishihara, T.; Yamanaka, H. Chem. Lett. 2000, 1360.
19. N2′ attack of palladium catalyst; see: (a) Elsevier: C. J.; Stehouwer, P. M.; Westmijze, H.; Vermeer, P. J. Org. Chem. 1983, 48, 1103. (b) Marshall, J. A.; Adams, N. D. J. Org. Chem. 1997, 62, 367. (c) Dixneuf, P.; Guyot, T.; Ness, M. D.; Roberts, S. M. Chem. Commun, 1997, 2083. (d) Konno, T.; Tanikawa, M.; Ishihara, T.; Yamanaka, H. Chem. Lett. 2000, 1360.
20. N2′ attack of palladium catalyst; see: (a) Elsevier: C. J.; Stehouwer, P. M.; Westmijze, H.; Vermeer, P. J. Org. Chem. 1983, 48, 1103. (b) Marshall, J. A.; Adams, N. D. J. Org. Chem. 1997, 62, 367. (c) Dixneuf, P.; Guyot, T.; Ness, M. D.; Roberts, S. M. Chem. Commun, 1997, 2083. (d) Konno, T.; Tanikawa, M.; Ishihara, T.; Yamanaka, H. Chem. Lett. 2000, 1360.
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27. Åkermark has reported changes in the syn/anti ratio of π-allylpalladium complexes by using various ligands: Sjögren, M.; Hansson, S.; Norrby, P.-O.; Åkermark, B. Organometallics 1992, 11, 3954.