使用手性铑（II）羧酸盐对硅烯醇醚进行催化对映选择性胺化反应：（-）-美他佐辛的不对称形式合成。
Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates: asymmetric formal synthesis of (-)-metazocine.
作者信息
Anada Masahiro, Tanaka Masahiko, Washio Takuya, Yamawaki Minoru, Abe Takumi, Hashimoto Shunichi
机构信息
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.
出版信息
Org Lett. 2007 Oct 25;9(22):4559-62. doi: 10.1021/ol702019b. Epub 2007 Sep 26.
Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate], Rh2(S-TFPTTL)4, is an exceptionally efficient catalyst for enantioselective aminations of silyl enol ethers derived from acyclic ketones or alpha,beta-enones with [N-(2-nitrophenylsulfonyl)imino]phenyliodinane (NsN=IPh), providing N-(2-nitrophenylsulfonyl)-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.
四[（N-四氟邻苯二甲酰基-（S）-叔亮氨酸根）]二铑（II），Rh2（S-TFPTTL）4，是一种极其高效的催化剂，用于由无环酮或α，β-烯酮衍生的硅基烯醇醚与[（N-（2-硝基苯磺酰基）亚氨基]苯基碘鎓（NsN=IPh）进行对映选择性胺化反应，能以高收率和高达95%ee的对映选择性提供N-（2-硝基苯磺酰基）-α-氨基酮。本催化方法的有效性已通过（-）-美他佐辛的不对称形式合成得到证明。
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