Mechanistic switch leading to highly efficient chirality transfer in Pd(0)-catalyzed coupling-cyclization of aryl iodides with 1:1 acid-base salts of 2,3-allenoic acids and L-(−)-cinchonidine or D-(+)-/L-(−)-α-methylbenzylamine. Enantioselective synthesis of highly optically active 3-aryl polysubstituted butenolides

Chemical Communications

Volumn 2, Issue 5, 2002, Pages 540-541

  Ma, Shengming ^a   Shi, Zhangjie ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; BENZYLAMINE DERIVATIVE; BUTENOLIDE; CINCHONIDINE; IODINE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; CYCLIZATION; ENANTIOSELECTIVITY; ISOMERISM; OPTICAL ROTATION; OXIDATION; REACTION ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 0037034884     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/b109645a     Document Type: Article

References (32)

1. R. D. Larock, B. Riefling and C. A. Fellows, J. Org. Chem., 1978, 43, 131 and the references cited therein.
2. Y. Chia, F. Chang, Y. Wu: Tetrahedron Lett. 1999 40 7513
3. S. Takahashi, K. Maeda, S. Hirota, T. Nakata: Org. Lett. 1999 1 2025
4. B. S. Siddiqui, F. Afshan, Farhana S. Faizi, S. N.-H. Naqvi, R. M. Tariq: J. Chem. Soc., Perkin Trans. 1 1999 2367
5. D. A. G. Cortez, J. B. Fermandes, P. C. Vieria, M. F. Das, G. F. Da Silva, A. G. Ferreira, Q. B. Cass, J. R. Pirani: Phytochmistry 1998 49 2493
6. H. Ostuka, K. Kotani, M. Bando, M. Kido, Y. Takeda: Chem. Pharm. Bull. 1998 46 1180
7. T. Ishikawa, K. Nishigaya, H. Uchikoshi, I. Chen: J. Nat. Prod. 1998 64 534
8. S. Driol, F. Felluga, C. Forzeto, P. Nitti, G. Pitacco, E. Valentin: J. Org. Chem. 1998 63 2385
9. S. Guo, L. Wang, D. Chen: India J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1997 36B 339
10. T. S. Brima, US 4,968,817, 1990:Chem. Abs. 1991 114 185246y
11. A. Tanabe, Jpn. Kokai Tokyo Koho JP 63,211,276 [88,211,276], 1988: Chem. Abs. 1989 110 94978q
12. G. C. M. Lee, Eur. Pat. EP. 372,940, 1990: Chem. Abs. 1990 113 19; 1137j
13. Y. Ducharme, J. Y. Gauthier, P. Prasit, Y. Leblanc, Z. Wang, S. Leger and M. Thrien, PCT Int. Appl. WO 95, 00,501, 1995: Chem. Abs. 1996 124 55954y
14. C. M. L. Gary and M. E. Gast, PCT Int. Appl. WO. 91 16,055, 1991: Chem. Abs. 1992 116 59197m
15. A. van Oeveren, B. L. Feringa: J. Org. Chem. 1996 61 2920
16. M. Renard, L. Ghosez: Tetrahedron Lett. 1999 40 6237
17. S. Tsuboi, J. Sakamoto, H. Yamashita, T. Sakai, M. Utaka: J. Org. Chem. 1998 63 1102
18. Q. Yu, Y. Wu, L. Xia, M. Tang, Y. Wu: Chem. Commun. 1999 129
19. T. Berkenbusch, R. Brckner: Tetrahedron 1998 54 1;1461
20. S. Ma, S. Wu: J. Org. Chem. 1999 64 9314
21. S. Ma, Z. Shi, Z. Yu: Tetrahedron 1999 55 1;2137
22. S. Ma, Z. Shi, Z. Yu: Tetrahedron Lett. 1999 40 2393
23. S. Ma, S. Zhao: J. Am. Chem. Soc. 1999 121 7943
24. S. Ma, Z. Zhang: Chem. Commun. 2000 117
25. S. Ma, L. Li: Org. Lett. 2000 2 941
26. A. S. K. Hashmi: Angew. Chem. Int. Ed. 2000 39 3590
27. S. Ma, Z. Shi: J. Org. Chem. 1998 63 6387
28. H.-J. Bestmann, H. Hartung: Chem. Ber. 1966 99 1198
29. H. D. Venkruijsse and L. Brandsma, Synthesis of Acetylenes, Allenes annd Cumulenes. A Laboratory Manual, Elsevier, Amsterdam, The Netherlands, 1981, p. 33
30. S. Ma, S. Wu: Chem. Commun. 2001 441
31. W. Runge, G. Kresze: Liebigs Ann. Chem. 1975 1361
32. S. R. Landor, The Chemistry of the Allenes, Academic Press, New York, 1982, vol. 3, pp. 587-590