2,3,4- or 2,3,5-trisubstituted furans: Catalyst-controlled highly regioselective ring-opening cycloisomerization reaction of cyclopropenyl ketones

Journal of the American Chemical Society

Volumn 125, Issue 41, 2003, Pages 12386-12387

  Ma, Shengming ^a   Zhang, Junliang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; CARBON; CHLORIDE; COPPER DERIVATIVE; CYCLOPROPANE DERIVATIVE; CYCLOPROPENE DERIVATIVE; FURAN DERIVATIVE; HALIDE; IODINE DERIVATIVE; KETONE DERIVATIVE; OXYGEN; PALLADIUM; PHENYL GROUP; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; CYCLIZATION; ELIMINATION REACTION; ISOMERISM; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY; STOICHIOMETRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0141988963     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036616g     Document Type: Article

References (19)

1. For a review, see: Baird, M. S. Cyclopropenes: Synthesis: By Construction of the System. Houben-Weyl; Thieme: Stuttgart, Germany, 1997; E17d/2, p 2695.
2. For reviews, see: (a) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77.
3. (b) Jennings, P. W.; Johnoson, L. L. Chem. Rev. 1994, 94, 2241.
4. (c) Baird, M. S. Cyclopropenes: Transformations. Houben-Weyl; Thieme: Stuttgart, Germany, 1997; E17d/2, p 2781.
5. (d) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295.
6. (a) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297.
7. (b) Liao, L.; Fox, J. M. J. Am. Chem. Soc. 2002, 124, 14322.
8. (c) Cho, S. H.; Liebeskind, L. S. J. Org. Chem. 1987, 52, 2631.
9. (a) Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 2000, 122, 978.
10. (b) Kubota, K.; Mori, S.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 1998, 120, 13334.
11. (c) Section IV.B.1 in ref 2d.
12. For a ligand effect on switching the regioselectivity in allylzincation of 1-trimethylsilyl (Ge, Sn)-cyclopropenone acetals, see: Nakamura, M.; Inoue, T.; Sato, A.; Nakamura, E. Org. Lett. 2000, 2, 2193.
13. For control of regioselectivity by the metallic complexes of different oxidation states, see: Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1991, 56, 6971.
14. Ma, S.; Zhang, J. Angew. Chem., Int. Ed. 2003, 42, 184.
15. (a) Mushak, P.; Battiste, M. A. J. Organomet. Chem. 1969, 17, P46.
16. (b) Battiste, M. A.; Friedrich, L. E.; Fiato, R. A. Tetrahedron Lett. 1975, 45.
17. The starting materials 1 were prepared in moderate yields by the rhodium-catalyzed cyclopropanation reaction of alkynes according to the following reference except that the corresponding diazo compounds were used instead of iodonium ylides, see: Batsila, C.; Kostakis, G.; Hadjiarapoglou, L. P. Tetrahedron Lett. 2002, 43, 5997.
18. int = 0.0555), no observation [I > 2σ(I)] 3776, parameters 425, CCDC 211695 contains the supplementary crystallographic data.
19. int = 0.0589), No Observation [1 > 2σ(I)] 2119, parameters 245, CCDC 211696 contains the supplementary crystallographic data.