A facile asymmetric synthesis of 1,2,3-substituted indenes

Journal of Organic Chemistry

Volumn 64, Issue 5, 1999, Pages 1733-1737

  Romines, Karen R ^a,b   Lovasz, Kristine D ^a   Mizsak, Stephen A ^a   Morris, Jeanette K ^a   Seest, Eric P ^a   Han, Fusen ^a   Tulinsky, John ^a   Judge, Thomas M ^a   Gammill, Ronald B ^a,c  

^a Medicinal Chemistry Research   (United States)

^b GLAXOSMITHKLINE   (United States)

^c PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; INDENE DERIVATIVE;

ACYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; NOTE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033525480     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9819638     Document Type: Note

References (23)

1. Heller, H. G. In Aromatic Compounds with Two Fused Carbocyclic Ring Systems: Benzocyclopropene, Benzocyclobutene, and Indene and their Derivatives, 2nd ed.; Correy, S., Ansell, M. F., Eds.; Rodd's Chemistry of Carbon Compounds; Elsevier: Amsterdam, The Netherlands, 1978; Vol. 3, Issue G.
2. (a) Liebeskind, L. S.; Gasdaska, J. R.; McCallum, J. S. J. Org. Chem. 1989, 54, 669.
3. (b) Robinson, N. P.; Main, L.; Nicholson, B. K. J. Organomet. Chem. 1989, 364, C37.
4. (c) Cambie, R. C.; Metzler, M. R.; Rutledge, P. S.; Woodgate, P. D. J. Organomet. Chem. 1992, 429, 41.
5. (a) Padwa, A.; Blacklock, T. J.; Getman, D.; Hatanaka, N. J. Am. Chem. Soc. 1977, 99, 2344.
6. (b) Semmelhack, M. F.; Ho, S.; Cohen, D.; Steigerwald, M.; Lee, M. C.; Lee, G.; Gilbert, A. M.; Wulff, W. D.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7108.
7. Gassman, P. G.; Ray, J. A.; Wenthold, P. G.; Mickelson, J. W. J. Org. Chem. 1991, 56, 5143.
8. Yamamura, K.; Miyake, H.; Seta, A. Bull. Chem. Soc. Jpn. 1986, 59, 3699.
9. Singh, G.; Ila, H.; Junjappa, H. Synthesis 1986, 744.
10. For example, see: (a) Weidler, A.-M.; Bergson, G Acta Chem. Scand. 1964, 18, 1483.
11. (b) Hussenius, A.; Matsson, O.; Bergson, G. J. Chem. Soc., Perkin Trans. 2 1989, 851.
12. Purchased from Aldrich Chemical Co.
13. For reviews, see: (a) Rossiter, B. E.; Swinge, N. M. Chem. Rev. 1992, 92, 771.
14. (b) Nicolas, E.; Russell, K. C.; Hruby, V. J. J. Org. Chem. 1993, 58, 766.
15. (a) A full account of this work, which was initially described in ref 10b, is currently under revision and will appear shortly,
16. (b) Judge, T. M.; Phillips, G.; Morris, J. K.; Lovasz, K. D.; Romines, K. R.; Luke, G. P.; Tulinsky, J.; Tustin, J. M.; Chrusciel, R. A.; Dolak, L. A.; Mizsak, S. A.; Watt, W.; Morris, J.; Vander Velde, S. L.; Strohbach, J. W.; Gammill, R. B. J. Am. Chem. Soc. 1997, 119, 3627.
17. (a) Nicholas, E.; Dharanipragada, R.; Toth, G.; Hruby, V. J. Tetrahedron Lett. 1989, 30, 6845.
18. (b) Qian, X.; Russell, K. D.; Boteju, L. W.; Hruby, V. J. Tetrahedron Lett. 1995, 51, 1033.
19. Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215.
20. R 14.70 min) were analyzed using a 0.46 × 25 cm Chiralcel OD-H column (elution of 0.5 mL/min with 5% 2-propanol/ 0.5% acetic acid/heptane, detection at 353 nm).
21. Seebach, D.; Hungerbühler, E.; Naef, R.; Schnurrenberger, P.; Weidmann, B.; Züger, M. Synthesis 1982, 138.
22. 2 substituent). An X-ray crystal structure was obtained of 20a to assign the absolute stereochemistry based on the known configuration of the C-3 ethyl substituent.
23. Synthesis and characterization of the enantiomers of compounds 3-5 have been previously described in ref 10b.