Stereocontrol of metal-catalyzed cycloaddition of carbonyl ylide with N- substituted maleimide

Tetrahedron Letters

Volumn 39, Issue 20, 1998, Pages 3165-3166

  Suga, Hiroyuki ^a,b   Ishida, Hajime ^a   Ibata, Toshikazu ^a  

^a OSAKA UNIVERSITY   (Japan)

^b SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 (METHOXYCARBONYL) ALPHA DIAZOACETOPHENONE; CARBONYL DERIVATIVE; COPPER; MALEIMIDE DERIVATIVE; METAL; UNCLASSIFIED DRUG; YTTERBIUM;

ARTICLE; CATALYSIS; CATALYST; DECOMPOSITION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032516374     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00449-3     Document Type: Article

References (11)

1. 2. a) Ueda, K.; Ibata, T.; Takebayashi, M. Bull. Chem. Soc. Jpn. 1972, 45, 2779.
2. b) Ibata, T.; Jitsuhiro, K. Bull. Chem. Soc. Jpn, 1979, 52, 3582.
3. c) Ibata, T.; Jitsuhiro, K.; Tsubokura, Y. Bull. Chem. Soc. Jpn., 1981, 54, 240.
4. d) Ibata, T.; Toyoda, J. Bull. Chem. Soc. Jpn. 1985, 55, 1787.
5. 3. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
6. 4. Padwa, A.; Austin, D. J.; Hornbuckle, S. F. J. Org. Chem. 1996, 61, 63.
7. 5. Doyle, M. P.; Forbes, D. C.; Protopopva, M. N.; Stanley, S. A.; Vasbinder, M. M.; Xavier, K. R. J. Org. Chem. 1997, 62, 7210.
8. 6. There are a few examples known that Lewis acids controlled regio- and/or stereoselectivity of dipolar cycloadditions. a) Kanemasa, S.; Uemura, T.; Wada, E.; Tetrahedron Lett. 1992, 33, 7889.
9. b) Kanemasa, S. Nishiuchi, M.; Kamimura, A.; Hori, K. J. Am. Chem. Soc., 1994, 116, 2324.
10. c) Gothelf, K. V.; Thomsen, I.; Jørgensen, K. A. J. Am. Chem. Soc., 1996, 118, 59. also see the references cited there in.
11. 7. Recently, intramolecular enantioselective cycloaddition of carbonyl ylide has been reported: Hodgson, D. M.; Stupple, P. A.; Johnstone, C. Tetrahedoron Lett., 1997, 38, 6471.