Three-component homo 3 + 2 dipolar cycloaddition. A diversity-oriented synthesis of tetrahydro-1,2-oxazines and FR900482 skeletal congeners.
[reaction: see text] 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.
Young
Ian S
IS
Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7.
Kerr
Michael A
MA