ENANTIOSELECTIVE SYNTHESIS OF HOMOALLYLIC AMINES - EVIDENCE OF REVERSIBLE ADDITION OF ALLYLZINC BROMIDE TO AROMATIC IMINES DERIVED FROM (S)-VALINE METHYL-ESTER AND (S)-VALINOL

被引:47
作者
BOCOUM, A [1 ]
SAVOIA, D [1 ]
UMANIRONCHI, A [1 ]
机构
[1] UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,VIA SELMI 2,I-40126 BOLOGNA,ITALY
关键词
D O I
10.1039/c39930001542
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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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页码:1542 / 1544
页数:3
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