Chiral photochemistry in a confined space: torquoselective photoelectrocyclization of pyridones within an achiral hydrophobic capsule

Sundaresan, Arun Kumar ; Gibb, Corinne L. D. ; Gibb, Bruce C. ; Ramamurthy, V. (2000) Chiral photochemistry in a confined space: torquoselective photoelectrocyclization of pyridones within an achiral hydrophobic capsule Tetrahedron, 65 (35). pp. 7277-7288. ISSN 0040-4020

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tet.2009.01.110

Abstract

Chiral induction during the photoelectrocyclization of pyridones included within octa acid (OA) capsule has been established. Chiral induction is brought about by a chiral auxiliary appended to the reactive pyridone moiety. Importantly, the same chiral auxiliary while ineffective in acetonitrile solution is found to be effective within the confined space of OA capsule. The diastereomeric excess of 92% obtained here is comparable only to that in solid state. OA capsule, we believe, provides restriction to the rotational motions of the reactant pyridone and chiral auxiliary and thus places the chiral auxiliary in a selective conformation with respect to the reactive pyridone part. A correlation between the position of the methyl group on the pyridone ring and diastereoselectivity was noted. Structures of the host-guest complexes were examined by H NMR and the data were used to obtain preliminary information concerning the mechanism of chiral induction within the confined spaces of OA capsule.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Host-guest; Chiral Photochemistry; Electrocyclization; Pyridones; Confined Space; Supramolecular Assemblies
ID Code:90040
Deposited On:04 May 2012 05:18
Last Modified:04 May 2012 05:18

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