Control of stereoselective protonation of enols

Journal of Organic Chemistry

Volumn 71, Issue 3, 2006, Pages 873-882

  Zimmerman, Howard E ^a   Cheng, Jie ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; CHARGE TRANSFER; ORGANIC COMPOUNDS; PH EFFECTS; PROTONS; STEREOCHEMISTRY;

ENOLS; INTERMOLECULAR PROTONATION; SILOXY ENOLIC MOIETY; STEREOSELECTIVE PROTONATION;

ALCOHOLS;

ACETIC ACID DERIVATIVE; FLUORIDE; KETONE DERIVATIVE;

ACIDITY; ARTICLE; CHEMICAL REACTION KINETICS; HYBRIDIZATION; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS; THEORETICAL STUDY;

ACETIC ACID; ALDEHYDES; AMINES; CARBOXYLIC ACIDS; COMPUTERS; ETHER, ETHYL; HYDROGEN-ION CONCENTRATION; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; METHYLATION; MOLECULAR STRUCTURE; PROTONS; STEREOISOMERISM;

EID: 32144458560     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051611i     Document Type: Article

References (17)

1. This is our publication 279.
2. For publication 278 and a preliminary report of some of our early results, see: Zimmerman, H. E.; Cheng, J. Org. Lett. 2005, 7, 2595-2597.
3. Zimmerman, H. E. J. Org. Chem. 1955, 20, 549-557.
4. (a) See ref 4b for early references.
5. (b) Zimmerman, H. E. Acc. Chem. Res. 1987, 20, 263-268.
6. (c) Zimmerman, H. E.; Wang, P. J. J. Org. Chem. 2003, 68, 9226-9232.
7. (a) Zimmerman, H. E.; Ignatchenko, A. J. Am. Chem. Soc. 1998, 120, 12992-12993.
8. (b) Zimmerman, H. E.; Ignatchenko, J. Org. Chem. 1999, 64, 6635-6645.
9. (a) Zimmerman, H. E.; Wang, P. Org. Lett. 2002, 4, 2593-2595.
10. (b) Zimmerman, H. E.; Wang, P. J. Org. Chem. 2002, 69, 9216-9226.
11. (a) Heathcock, C. H.; Ellis, J. E.; Mcmurry, J. E.; Coppolino, A. Tetrahedron Lett. 1971, 52, 4995-4996.
12. (b) Banerjee, D. K.; Angadi, V. B. Tetrahedron 1965, 21, 281-289.
13. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, C.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskora, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gau.isian 98, Revision A.9; Gaussian, Inc.: Pittsburgh. PA, 1998.
14. The size of the molecular systems studied, their considerable number, and the number of points needed in some of the computations necessitated a compromise in choice of the quantum mechanical method and basis set used. Those selected represent a practical and respectable choice leading to more than qualitative results.
15. (a) Paufler, R.; Zimmerman, H. E. Unpublished results. Paufler, R. Ph.D. Dissertation. Ketonization of a Dienol and the Synthesis of Bicyclo-[2.2.2]- Octatriene (Barrelene). Northwestern University, 1960; p 16.
16. (b) Malhotra, S. K.; Ringold, H. J. Am. Chem. Soc. 1965, 87, 3228-3226.
17. Quantum Mechanics for Organic Chemists; Zimmerman, H. E.; Academic Press: New York, 1975.