2000 stereochemistry

stereochemistry (general, optical resolution)O 0030

48 - 028A General Method for the Vinylation of Nitrones. Synthesis of AllylHydroxylamines and Allyl Amines. — A method for the vinylation ofnitrones of type (I), (VII), and (X) is given. In the case of α-alkoxy nitrones,a complete diastereofacial discrimination is observed; the opposite stereochem-istry is observed when the reaction is performed in the presence of Et2AlCl.α-Amino nitrones preferentially give syn adducts with the only exceptionof (VII). The obtained allyl hydroxylamines can be easily reduced to thecorresponding synthetically valuable allyl amines, cf. compounds (V) and (VI).— (MERINO, PEDRO; ANORO, SONIA; FRANCO, SANTIAGO; GASCON,JOSE M.; MARTIN, VICTOR; MERCHAN, FRANCISCO L.; REVUELTA,JULIA; TEJERO, TOMAS; TUNON, VICTORIA; Synth. Commun. 30 (2000)16, 2989-3021; Dep. Quim. Org., Inst. Cienc. Mater. Aragon, CSIC-Univ.Zaragoza, E-50009 Zaragoza, Spain; EN)

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