ENANTIOSELECTIVE SYNTHESIS OF HOMOALLYLIC AMINES - EVIDENCE OF REVERSIBLE ADDITION OF ALLYLZINC BROMIDE TO AROMATIC IMINES DERIVED FROM (S)-VALINE METHYL-ESTER AND (S)-VALINOL
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BOCOUM, A
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UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,VIA SELMI 2,I-40126 BOLOGNA,ITALYUNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,VIA SELMI 2,I-40126 BOLOGNA,ITALY
BOCOUM, A
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SAVOIA, D
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UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,VIA SELMI 2,I-40126 BOLOGNA,ITALYUNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,VIA SELMI 2,I-40126 BOLOGNA,ITALY
SAVOIA, D
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]
UMANIRONCHI, A
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UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,VIA SELMI 2,I-40126 BOLOGNA,ITALYUNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,VIA SELMI 2,I-40126 BOLOGNA,ITALY
UMANIRONCHI, A
[1
]
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[1] UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,VIA SELMI 2,I-40126 BOLOGNA,ITALY
The reaction of aromatic and aliphatic imines derived from (S)-valine methyl ester and (S)-valinol with allyl bromide and zinc in tetrahydrofuran affords homoallylic amines with up to 100% diastereoisomeric excess (d.e.), but in the case of the aromatic imines the diastereoselectivity is lowered by increasing the reaction time, owing to the reversibility of the allylation reaction.
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FAC SCI & TECH NANTES,SYNTH ORGAN LAB,CNRS,URA 475,2 RUE DE LA HOUSSINIERE,F-44072 NANTES 03,FRANCEFAC SCI & TECH NANTES,SYNTH ORGAN LAB,CNRS,URA 475,2 RUE DE LA HOUSSINIERE,F-44072 NANTES 03,FRANCE
DEMBELE, YA
BELAUD, C
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FAC SCI & TECH NANTES,SYNTH ORGAN LAB,CNRS,URA 475,2 RUE DE LA HOUSSINIERE,F-44072 NANTES 03,FRANCEFAC SCI & TECH NANTES,SYNTH ORGAN LAB,CNRS,URA 475,2 RUE DE LA HOUSSINIERE,F-44072 NANTES 03,FRANCE
BELAUD, C
VILLIERAS, J
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FAC SCI & TECH NANTES,SYNTH ORGAN LAB,CNRS,URA 475,2 RUE DE LA HOUSSINIERE,F-44072 NANTES 03,FRANCEFAC SCI & TECH NANTES,SYNTH ORGAN LAB,CNRS,URA 475,2 RUE DE LA HOUSSINIERE,F-44072 NANTES 03,FRANCE
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FAC SCI & TECH NANTES,SYNTH ORGAN LAB,CNRS,URA 475,2 RUE DE LA HOUSSINIERE,F-44072 NANTES 03,FRANCEFAC SCI & TECH NANTES,SYNTH ORGAN LAB,CNRS,URA 475,2 RUE DE LA HOUSSINIERE,F-44072 NANTES 03,FRANCE
DEMBELE, YA
BELAUD, C
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FAC SCI & TECH NANTES,SYNTH ORGAN LAB,CNRS,URA 475,2 RUE DE LA HOUSSINIERE,F-44072 NANTES 03,FRANCEFAC SCI & TECH NANTES,SYNTH ORGAN LAB,CNRS,URA 475,2 RUE DE LA HOUSSINIERE,F-44072 NANTES 03,FRANCE
BELAUD, C
VILLIERAS, J
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FAC SCI & TECH NANTES,SYNTH ORGAN LAB,CNRS,URA 475,2 RUE DE LA HOUSSINIERE,F-44072 NANTES 03,FRANCEFAC SCI & TECH NANTES,SYNTH ORGAN LAB,CNRS,URA 475,2 RUE DE LA HOUSSINIERE,F-44072 NANTES 03,FRANCE