Pd-catalyzed asymmetric hydrogenation of α-fluorinated iminoesters in fluorinated alcohol:: A new and catalytic enantioselective synthesis of fluoro α-amino acid derivatives

Pd-catalyzed asymmetric hydrogenation of α-fluorinated iminoesters in fluorinated alcohol:: A new and catalytic enantioselective synthesis of fluoro α-amino acid derivatives
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DOI:
10.1021/ol0002471
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发表时间:
2001-02-08
期刊:
影响因子:
5.2
通讯作者:
Uneyama, K
Uneyama, K
中科院分区:
化学1区
文献类型:
--
作者:
Abe, H;Amii, H;Uneyama, K

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在氢气压力下,催化量的三氟乙酸钯(II)和2,2 ′-双(二苯基膦基)-1,1 ′-联萘(BINAP)促进α-氟化亚氨基酯的不对称氢化,得到高度对映体富集的β-氟化α-氨基酯。采用含氟醇如2,2,2-三氟乙醇可使收率和ee值提高到91%以上。
[GRAPHICS]Under hydrogen pressure, a catalytic amount of palladium(II) trifluoroacetate and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) promoted asymmetric hydrogenation of alpha -fluorinated iminoesters to afford highly enantioenriched beta -fluorinated alpha -amino esters. The yield and ee were much improved by employing fluorinated alcohols such as 2,2,2-trifluoroethanol (up to 91% eel.