Reactions of Arylaldehydes and N-Sulfonated Imines with Dimethyl Acetylenedicarboxylate Catalyzed by Nitrogen and Phosphine Lewis Bases

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4273-4276

  Li, Chao Qun ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; BASE; IMINE; NITROGEN; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CRYSTAL STRUCTURE; X RAY CRYSTALLOGRAPHY;

EID: 0344065767     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0354324     Document Type: Article

References (13)

1. Nair, V.; Sreekanth, A. R.; Vinod, A. U. Org. Lett. 2001, 3, 3495 and references therein.
2. (a) Shi, M.; Xu, Y.-M. Chem. Commun. 2001, 1876.
3. (b) Shi, M.; Xu, Y.-M. Eur. J. Org. Chem. 2002, 696.
4. (c) Shi, M.; Xu, Y.-M.; Zhao, G.-L.; Wu, X.-F. Eur. J. Org. Chem. 2002, 3666.
5. (d) Shi, M.; Xu, Y.-M. J. Org. Chem. 2003, 68, 4784.
6. w = 0.1751.
7. Phosphine Lewis base-catalyzed [3 + 2] cycloaddition of acetylenedicarboxylate with N-tosylated imines has been reported. Please see: (a) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. (b) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031. (c) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
8. Phosphine Lewis base-catalyzed [3 + 2] cycloaddition of acetylenedicarboxylate with N-tosylated imines has been reported. Please see: (a) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. (b) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031. (c) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
9. Phosphine Lewis base-catalyzed [3 + 2] cycloaddition of acetylenedicarboxylate with N-tosylated imines has been reported. Please see: (a) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. (b) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031. (c) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
10. w = 0.1751.
11. Tertiary phosphine-catalyzed lactone formation from electron-deficient carbonyl compounds and DMAD has been reported. Nozaki, K.; Sato, N.; Ikeda, K.; Takoya, H.J. Org. Chem. 1996, 61, 4516.
12. w = 0.0637.
13. These electron-deficient alkynes such as phenylacetylene, methyl propiolate, and 3-butyn-2-one are labile at 60°C in THF. Therefore, these reactions were carried out at room temperature.