Enantioselective Diels-Alder reactions between cyclopentadiene and α,β-acetylenic aldehydes catalyzed by a chiral super Lewis acid

Tetrahedron Letters

Volumn 38, Issue 33, 1997, Pages 5755-5758

  Corey, E J ^a   Lee, Thomas W ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; NORBORNANE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

BETULACEAE;

EID: 0030814062     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01287-2     Document Type: Article

References (16)

1. For example, see (a) Ishihara, K.; Gao, Q.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10412.
2. (b) Corey, E. J.; Loh, T.-P.; Roper, T. D.; Azimioara, M. D.; Noe, M. C. J. Am. Chem. Soc. 1992, 114, 8290.
3. (c) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798.
4. (d) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049.
5. (e) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611.
6. (f) Corey, E. J.; Letavic, M. A. J. Am. Chem. Soc. 1995, 117, 9616.
7. Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502.
8. All silylpropynals were prepared by analogy to a known two-step synthesis of 3-trimethylsilyl-2-propynal, see (a) Danheiser, R. L.; Carini, D. J.; Fink, D. M.; Basak, A. Tetrahedron 1983, 39, 935.
9. (b) Harris, N. J.; Gajewski, J. J. J. Am. Chem. Soc. 1994, 116, 6121.
10. f impurity can easily be distinguished from the desired product (baseline).
11. +): 411.1710; found 411.1714.
12. The X-ray crystallographic analysis was carried out by Mr. Michael Grogan of this laboratory. Detailed X-ray crystallographic data are available from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
13. (a) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748.
14. 2 in DMF at room temperature.
15. See also Corey, E. J.; Barnes-Seeman, D.; Lee, T. W. Tetrahedron Letters 1997, 38, 1699.
16. This research was supported by grants from the National Science Foundation and the National Institutes of Health. T.W.L. is a Graduate Fellow of the National Science Foundation.