Cation-π interactions as a tool to enhance the power of a chiral auxiliary during asymmetric photoreactions within zeolites

Chemical Communications

Volumn , Issue 1, 2003, Pages 116-117

  Kaanumalle, Lakshmi S ^a   Sivaguru, J ^a   Arunkumar, N ^a   Karthikeyan, S ^a   Ramamurthy, V ^a  

^a Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; ZEOLITE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL PARAMETERS; CHIRALITY; PHOTOREACTIVITY;

EID: 0037222158     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b209810e     Document Type: Article

References (6)

1. All zeolites used in this study were procured from Zeolyst International and were activated at 500°C prior to use. Reactants were introduced into the zeolite by stirring the zeolite (300 mg) and the reactant (∼5 mg) together in hexane. The loading level was generally one molecule per four supercages. By GC analysis of the supernatant, it was made sure that all the reactants were adsorbed onto the zeolite. Following irradiation of the zeolite-hexane slurry the products were isolated by extraction of the zeolite with either tetrahydrofuran, acetonitrile or ether and analyzed by GC or HPLC. The analytical columns used were the following: 1a and 1c: β-dex-350 (GC); 1b and 1d: Chiralpack ADRH (HPLC); 3a, 3c and 3d SE-30 (GC); 3b: Chiralpack ADRH (HPLC); 5a: Chiralcel OD (HPLC); 5b and 5c: Chiralpack ADRH (HPLC); 5d: Chiralcel OJ (HPLC).
2. A. Joy and V. Ramamurthy, Chem. Eur. J., 2000, 6, 1287-1293.
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4. N. Arunkumar, K. Wang, V. Ramamurthy and J. R. Scheffer, Org. Lett., 2002, 4, 1443-1446.
5. Gaussian 98, Revision A.9, Gaussian Incorporation, Pittsburgh, PA, 1998.
6. J. C. Ma and D. A. Dougherty, Chem. Rev., 1997, 97, 1303-1324.