LiClO4- or LiOTf-accelerated 1,3-dipolar cycloaddition reactions: a facile synthesis of cis-fused chromano[4,3-c]isoxazoles

Yadav, J. S. ; Reddy, B. V. S. ; Narsimhaswamy, D. ; Narsimulu, K. ; Kunwar, A. C. (2003) LiClO4- or LiOTf-accelerated 1,3-dipolar cycloaddition reactions: a facile synthesis of cis-fused chromano[4,3-c]isoxazoles Tetrahedron Letters, 44 (18). pp. 3697-3700. ISSN 0040-4039

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

Related URL: http://dx.doi.org/10.1016/S0040-4039(03)00682-8

Abstract

Acetonitrile solutions of lithium perchlorate or lithium triflate are found to accelerate considerably the intramolecular 1,3-dipolar cycloaddition reactions of nitrones derived in situ from hydroxylamines and the O-prenyl derivatives of salicylaldehydes to afford enhanced rates and improved yields of tetrahydrochromano[4,3-c]isoxazole derivatives with high diastereoselectivity. The stereochemistry of the products has been assigned by using extensive NMR studies.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Lithium Salts; Nitrones; Intramolecular Cycloaddition; Chromanoisoxazoles
ID Code:58895
Deposited On:02 Sep 2011 03:18
Last Modified:02 Sep 2011 03:18

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