Catalytic enantioselective Amination of silyl enol ethers using chiral Dirhodium(II) carboxylates: Asymmetric formal synthesis of (-)-metazocine

被引：91

作者：

Anada, Masahiro ^{[1
]}

Tanaka, Masahiko ^{[1
]}

Washio, Takuya ^{[1
]}

Yamawaki, Minoru ^{[1
]}

Abe, Takumi ^{[1
]}

Hashimoto, Shunichi ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 22期

关键词：

D O I：

10.1021/ol702019b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[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.

引用

页码：4559 / 4562

页数：4

共 51 条

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