Three-Component Homo 3 + 2 Dipolar Cycloaddition. A Diversity-Oriented Synthesis of Tetrahydro-1,2-oxazines and FR900482 Skeletal Congeners
- 13 December 2003
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (1) , 139-141
- https://doi.org/10.1021/ol0362919
Abstract
The reaction of nitrones, formed in situ by reaction of hydroxylamines with aldehydes, with 1,1-cyclopropanediesters results in the formation of tetrahydro-1,2-oxazines via a homo 3 + 2 dipolar cycloaddition. This three-component coupling allows for the formation of a diverse array of cycloadducts with excellent diastereoselectivity (>95%) and yields (66−96%). The procedure has been used in the two-step preparation of congeners of the FR900482 skeleton.Keywords
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