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3-(N,N-Diacylamino)quinazolin-4(3H)-ones as enantioselective acylating agents for amines

✍ Scribed by Abdullah G Al-Sehemi; Robert S Atkinson; John Fawcett; David R Russell


Book ID
104210031
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
106 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis


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).


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ChemInform Abstract: 3-(N,N-Diacylamino)
✍ Abdullah G. Al-Sehemi; Robert S. Atkinson; John Fawcett; David R. Russell πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 30 KB πŸ‘ 1 views

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