Catalytic asymmetric synthesis of α,α,α-trifluoromethylamines by the copper-catalyzed nucleophilic addition of diorganozinc reagents to imines

Catalytic asymmetric synthesis of α,α,α-trifluoromethylamines by the copper-catalyzed nucleophilic addition of diorganozinc reagents to imines
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DOI:
10.1021/ol0607847
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发表时间:
2006-06-22
期刊:
影响因子:
5.2
通讯作者:
Charette, Andre B.
Charette, Andre B.
中科院分区:
化学1区
文献类型:
--
作者:
Lauzon, Caroline;Charette, Andre B.

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本文报道了铜催化的二有机锌试剂与N-膦酰亚胺的不对称加成反应,合成了手性α,α,α-三氟甲基胺。由相应的半缩醛原位生成的三氟甲基酮亚胺以高产率(71-89%)和优异的对映体控制(91- 99%ee)得到手性酰胺。
A copper-catalyzed asymmetric addition of diorganozinc reagents to N-phosphinoylimines has been developed for the synthesis of chiral alpha, alpha, alpha-trifluoromethylamines. The trifluoromethyl ketimines, generated in situ from the corresponding hemiaminals, led to the chiral amides in high yields (71-89%) and excellent enantiocontrol (91-99% ee).