Enantioselective organo-singly occupied molecular orbital catalysis: The carbo-oxidation of styrenes

Journal of the American Chemical Society

Volumn 130, Issue 49, 2008, Pages 16494-16495

  Graham, Thomas H ^a   Jones, Casey M ^a   Jui, Nathan T ^a   MacMillan, David W C ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; STYRENE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRAL CHROMATOGRAPHY; CHIRALITY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; STEREOCHEMISTRY;

ALDEHYDES; CATALYSIS; OXIDATION-REDUCTION; STEREOISOMERISM; STYRENE; SUBSTRATE SPECIFICITY;

EID: 57549095938     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8075633     Document Type: Article

References (13)

1. MacMillan, D. W. C. Nature 2008, 405, 304.
2. Beeson, T. D.; Mastracchio, A.; Hong, J. B.; Ashton, K.; MacMillan, D. W. C. Science 2007, 316, 582.
3. Narasaka, K.; Okauchi, T.; Tanaka, K.; Murakami, M. Chem. Lett. 1992, 2099.
4. Jang, H. Y.; Hong, J. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2008, 130, 398.
5. Kim, H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2007, 129, 398.
6. It is important to note that a noncatalytic, non-enantioselective intermolecular alkylation of malonate esters using styrene has been accomplished under oxidative conditions: Citterio, A.; Sebastiano, M.; Nicolini, R.; Santi, R. Synlett 1990, 42.
7. DFT calculations performed using B3LYP/6-311+G(2d,p)//B3LYP/6-31G(d)(see ref 2).
8. Nair, V.; Deepthi, A. Chem. Rev. 2007, 107, 1862.
9. (a) Auricchio, S.; Ricca, A. Tetrahedron 1987, 43, 3983.
10. (b) Baldwin, S. W.; Long, A. Tetrahedron Lett. 2001, 42, 5343.
11. Boivin, T. L. B. Tetrahedron 1987, 43, 3309.
12. Cainelli, G.; Manescalchi, F.; Martelli, G.; Panunzio, M.; Plessi, L. Tetrahedron Lett. 1985, 26, 3369.
13. We were unable to separate the nitrate ester diastereomeric adducts prior to heterocyclic ring formation.