Sensitivity of substitution to the extent of self-immolative chirality transfer during reaction cascades originating from squarate esters

Journal of Organic Chemistry

Volumn 62, Issue 6, 1997, Pages 1730-1736

  Paquette, Leo A ^a   Kuo, Lung Huang ^a   Hamme II, Ashton T ^a   Kreuzholz, Rüdiger ^a   Doyon, Julien ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0030894357     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962182e     Document Type: Article

References (15)

1. Paquette, L. A.; Morwick, T. M. J. Am. Chem. Soc. 1997, 119, 1230 and relevant references cited therein.
2. (a) Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 2099.
3. (b) Thomas, B. E., IV; Evanseck, J. D.; Houk, K. N. J. Am. Chem. Soc. 1993, 115, 4165.
4. (c) Dolbier, W. R., Jr.; Koroniak, H.; Houk, K. N.; Sheu, C. Acc. Chem. Res. 1996, 29, 471.
5. Paquette, L. A.; Hamme, A. T., II; Kuo, L. H.; Doyon, J.; Kueuzholz, R. J. Am. Chem. Soc. 1997, 119, 1242.
6. (a) Paquette, L., A.; Doyon, J. J. Am. Chem. Soc. 1995, 117, 6799.
7. (b) Paquette, L., A.; Doyon, J. J. Org. Chem. 1997, 62, 1723.
8. Johnson, C. R.; Sakaguchi, H. Synlett 1992, 813.
9. (a) Corey, E. J.; Chen, C.-P.; Reichard, G. A. Tetrahedron Lett. 1989, 30, 5547.
10. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925.
11. Corey, E. J.; Srinivas Rao, K. Tetrahedron Lett. 1991, 32, 4623.
12. Paquette, L. A.; Heidelbaugh, T. M. Org. Synth. 1996, 73, 44.
13. (a) Luche, J.-L. J. Am. Chem. Soc. 1978, 100, 2226.
14. (b) Luche, J.-L.; Rodriquez-Hahn, L.; Crabbé, P. Chem. Commun. 1978, 601.
15. The authors have deposited the atomic coordinates for the X-ray structures with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.