Inversion of the direction of stereoinduction in the coupling of chiral γ,δ-unsaturated fischer carbene complexes with o-ethynylbenzaldehyde

Organic Letters

Volumn 4, Issue 13, 2002, Pages 2121-2124

  Ghorai, Binay K ^a   Menon, Suneetha ^a   Lee Johnson, Dennis ^a   Herndon, James W ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; BENZALDEHYDE DERIVATIVE; CARBENE; DRUG DERIVATIVE; ETHYNYLBENZALDEHYDE; HYDROCARBON; METHANE; STEROID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; STEREOISOMERISM; SYNTHESIS; THERMODYNAMICS;

ALKYNES; BENZALDEHYDES; HYDROCARBONS; KINETICS; METHANE; MODELS, MOLECULAR; STEREOISOMERISM; STEROIDS; THERMODYNAMICS;

EID: 0037182721     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025808y     Document Type: Article

References (20)

1. Ghorai, B. K.; Herndon, J. W.; Lam, Y. F. Org. Lett. 2001, 3, 3535-3538.
2. Intramolecular Diels-Alder reactions of isobenzofurans are generally exo selective. (a) Meegalla, S. K.; Rodrigo, R. Synthesis 1989, 942-944.
3. (b) Yamaguchi, Y.; Yamada, H.; Hayakawa, K.; Kanematsu, K. J. Org. Chem. 1987, 52, 2040-2046.
4. Tobia, D.; Rickborn, B. J. Org. Chem. 1987, 52, 2611-2615.
5. For a discussion of the utility of this class of compounds, see: Nicolaou, K. C.; Zhong, Y. L.; Baran, P. S.; Sugita, S. Angew. Chem., Int. Ed. 2001, 40, 2145-2149.
6. This carbene-complex-forming step has previously been reported. Moser, W. H.; Hegedus, L. S. J. Am. Chem. Soc. 1996, 118, 7873-7880.
7. Pitteloud, R.; Petrilka, M. Helv. Chim. Acta 1979, 62, 1319-1325.
8. Related intramolecular Diels-Alder reactions of simple furans afford predominantly the equatorial isomer. (a) Woo, S. Keay, B. A. Tetrahedron: Asymmetry 1994, 5, 1411-1414.
9. (b) Rogers, C.; Keay, B. A. Tetrahedron Lett. 1991, 32, 6477-6880.
10. (c) Ferringa, B. L.; Gelling, O. J.; Meesters, L. Tetrahedron Lett. 1990, 31, 7201-7204.
11. (d) Sader-Bakoumi, L.; Charton, O.; Kunesch, N.; Tillequin, F. Tetrahedron 1998, 54, 1773-1782.
12. (e) Hudlicky, T.; Butora, G.; Fearnley, S. P.; Gum. A. G.; Persichini, P. J., III; Stabile, M. R.; Merola, J. S. J. Chem. Soc., Perkin Trans. 1 1995, 2393-2398.
13. (f) De Geyter, T.; Cauwberghs, S.; De Clercq, P. J. Bull. Soc. Chim. Belg. 1994, 103, 433-443.
14. (g) Metz, P.; Stölting, J.; Läge, M.; Krebs, B. Angew. Chem., Int. Ed. Engl. 1994, 33, 2195-2197.
15. (h) Meiners, U.; Cramer, E.; Froehlich, R.; Wibbeling, B.; Metz, P. Eur. J. Org. Chem. 1998, 2073-2078.
16. (i) Woo, S.; Keay, B. A. Synlett 1996, 135-137.
17. The stereochemistry was assigned on the basis of coupling constants between protons at stereogenic centers (see Supporting Information). For stereochemical assignments in similar ring systems, see: Piers, E.; Llinas-Brunet, M.; O'Balla, R. M. Can. J. Chem. 1993, 71, 1484-1494.
18. (a) Grieco, P. A.; Kaufman, M. D.; Daeuble, J. F.; Saito, N. J. Am. Chem. Soc. 1996, 118, 2095-2096.
19. (b) Blond, A.; Paltzer, N.; Guy, A.; D'Hotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283-293.
20. The program MacSaprtan Pro v. 1.04 was utilized in this study.