Efficient Nazarov Cyclizations of 2-Alkoxy-1,4-pentadien-3-ones

Organic Letters

Volumn 5, Issue 26, 2003, Pages 4931-4934

  Liang, Guangxin ^a   Gradl, Stefan N ^a   Trauner, Dirk ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANONE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0346025411     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036019z     Document Type: Article

References (16)

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3. (c) Santellirouvier, C.; Santelli, M. Synthesis (Stuttgart) 1983, 429-442.
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11. Denmark, S. E.; Habermas, K. L.; Hite, G. A. Helv. Chim. Acta 1988, 71, 168-94. For an alternative synthesis of 9r, see: Kwon, H. B.; McKee, B. H.; Stille, J. K. J. Org. Chem. 1990, 55, 3114-3118.
12. Concomitant to our work, the Tius group has studied Nazarov cyclizations of 2-alkoxy-1,4-penten-3-ones and catalytic asymmetric variants thereof. Tius, M. A.; Bee, C.; Leclerc, E. Org. Lett. 2003, 5, 4927-4930. For a related system, see: He, W.; Sun, X.; Frontier, A. J. J. Am. Chem. Soc. 2003, 725, 14278-14279.
13. Concomitant to our work, the Tius group has studied Nazarov cyclizations of 2-alkoxy-1,4-penten-3-ones and catalytic asymmetric variants thereof. Tius, M. A.; Bee, C.; Leclerc, E. Org. Lett. 2003, 5, 4927-4930. For a related system, see: He, W.; Sun, X.; Frontier, A. J. J. Am. Chem. Soc. 2003, 725, 14278-14279.
14. Compound 10p has been previously described: Katritzky, A. R.; Zhang, G. F.; Jiang, J. L. J. Org. Chem. 1995, 60, 7605-7611.
15. For the use of scandium pybox complexes in asymmetric synthesis, see: (a) Evans, D. A.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10162-10163. (b) Evans, D. A.; Masse, C. E.; Wu, J. Org. Lett. 2002, 4, 3375-3378.
16. For the use of scandium pybox complexes in asymmetric synthesis, see: (a) Evans, D. A.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10162-10163. (b) Evans, D. A.; Masse, C. E.; Wu, J. Org. Lett. 2002, 4, 3375-3378.