Journal
TETRAHEDRON LETTERS
Volume 43, Issue 46, Pages 8273-8275Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(02)02019-1
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A novel access to 1,4-benzodiazepin-2-ones starting from glycine and alanine derivatives is described. The key cyclization step was performed by the action of phenyliodine(III)bis(trifluoroacetate) (PIFA) on the corresponding methoxyamide derivatives leading to the C(9a)-N(1) bond construction. This strategy avoids the necessity of additional functionalization on the phenyl ring and facilitates the access to a number of 1,4-benzodiazepine derivatives. Additionally, no racemization in the cyclization step was observed starting from optically pure (S)-alanine ester. (C) 2002 Elsevier Science Ltd. All rights reserved.
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