Journal
TETRAHEDRON
Volume 60, Issue 10, Pages 2247-2257Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.01.018
Keywords
acyl migration; urea; alpha-aminoorganostannanes; alpha-aminoorganolithiums
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Transmetalation of urea derivatives of alpha-aminoorganostannanes with alkyllithiums provides alpha-aminoorganolithiums which undergo rapid N to C acyl migration to afford alpha-aminocarboxamides. The stereochemical course of the transmetalation/migration process depends on the substituents on the urea and varies from complete retention of configuration to complete racemization. (C) 2004 Elsevier Ltd. All rights reserved.
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