Journal
TETRAHEDRON LETTERS
Volume 41, Issue 13, Pages 2239-2242Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(00)00138-6
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The presence of an N-N chiral axis in a 3-(N-benzoyl-N-isobutanoyl)aminoquinazolin-4(3H)-one (DAQ) bearing a chiral substituent in the 2-position of the quinazolinone allows separation of two enantiopure diastereoisomers; one of these diastereoisomers reacts with racemic 2-methylpiperidine to give (R)(+)-1-benzoyl-2-methylpiperidine (95% ee) and (S)-2-methylpiperidine (91% ee) even using stoichiometric quantities of reagents (1 equiv. DAQ: 2 equiv. amine). (C) 2000 Elsevier Science Ltd. All rights reserved.
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