Catalytic enantioselective Amination of silyl enol ethers using chiral Dirhodium(II) carboxylates: Asymmetric formal synthesis of (-)-metazocine
Catalytic enantioselective Amination of silyl enol ethers using chiral Dirhodium(II) carboxylates: Asymmetric formal synthesis of (-)-metazocine
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DOI：
10.1021/ol702019b
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发表时间：
2007-10-25
期刊：
影响因子：
5.2
通讯作者：
Hashimoto, Shunichi
中科院分区：
文献类型：
--
作者：
Anada, Masahiro;Tanaka, Masahiko;Hashimoto, Shunichi
[图形]四（II）四[N-四氟苯甲酰-(S)-叔leucinate]， Rh-2(S- fpttl)(4)，是一种非常有效的催化剂，用于由无环酮或与[N-（2-硝基苯基磺酰基）亚胺]苯基碘烷（NsN=IPh）衍生的硅基烯醚的对映选择性胺化，以高产率提供N-（2-硝基苯基磺酰基）α -氨基酮，其对映选择性高达95% ee。目前的催化方案的有效性已经证明了(-)-甲他唑辛的不对称形式合成。
[GRAPHICS]Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate], Rh-2(S-FPTTL)(4), is an exceptionally efficient catalyst for enantioselective aminations of silyl enol ethers derived from acyclic ketones or a,beta-enones with [N-(2-nitrophenyisulfonyl)imino]phenyliodinane (NsN=IPh), providing N-(2-nitrophenyisulfonyl)-alpha-amino ketones in high yields and with enantioselectivities of up to 95% ee. The effectiveness of the present catalytic protocol has been demonstrated by an asymmetric formal synthesis of (-)-metazocine.