60073-34-9Relevant academic research and scientific papers
Resolution of β-unsaturated amines with isopropylidene glycerol hydrogen phthalate
Pallavicini, Marco,Valoti, Ermanno,Villa, Luigi,Piccolo, Oreste
, p. 4017 - 4025 (2007/10/03)
1-Phenyl-2-propenylamine 2, 1-phenyl-2-propinylamine 3, 1-(1-cyclohexenyl)ethylamine 4, (E)-2-ethylidenecyclohexylamine 5 and α-methylallylamine hydrochloride 6 were selected as candidates for resolution with isopropylidene glycerol hydrogen phthalate 1, previously described as an efficient resolving agent of 1-arylalkylamines. With only the exception of 5, all these substrates were resolved by (S)-1. In particular both the enantiomers of 2 and 3 were obtained in excellent yields and with very high enantiomeric excesses. The absolute configurations of non-racemic forms of 2, 3 and 4, not prepared before except those of 3, were established by correlation with the respective hydrogenation products. The enantiomeric excesses of all the resolved substrates were accurately determined by chiral HPLC analysis. The fact that 1 resolves 4 and 6 but not their saturated analogues and shows higher efficiency in resolving 2 and 3 than 1-phenylpropylamine indicates the positive influence of the presence of β-unsaturation on the resolvability of aminic substrates with such an acid. Copyright (C) 2000 Elsevier Science Ltd.
HYDROBORATION D'AZIRIDINES ETHYLENIQUES. SYNTHESE D'AZA-1 BICYCLO ALCANES
Chaabouni, Refaat,Laurent, Andre,Marquet, Bernard
, p. 877 - 885 (2007/10/02)
Hydroboration of aziridines having a β or γ-double bond 3b, 3c, 4b, 7c and 8 yields after oxydation, the expected hydroxy aziridines 11b, 11c, 12b, 13 and 14, which were cyclized by reaction with PPh3/Br2 to give 1-aza bicycloalkanes 23b, 24b, 25c, 26 and 27.The hydroboration of 2-vinyl aziridines 3a, 4a and 7a give Z-allylic amines 16aZ, 17aZ and 18Z.The use of 9-BBN or 2-vinyl substituated aziridines provides the β-hydroxy aziridines 19, 20 and 21.
