Catalytic Enantioselective Intermolecular Cycloaddition of Diazodiketoester-Derived Carbonyl Ylides with Indoles Using Chiral Dirhodium(II) Carboxylates

被引：65

作者：

Shimada, Naoyuki ^{[1
]}

Oohara, Tadashi ^{[1
]}

Krishnamurthi, Janagiraman ^{[1
]}

Nambu, Hisanori ^{[1
]}

Hashimoto, Shunichi ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 23期

关键词：

ASYMMETRIC TOTAL-SYNTHESIS; ALPHA-DIAZO KETONES; 1,3-DIPOLAR CYCLOADDITION; INTRAMOLECULAR CYCLOADDITION; RHODIUM CARBENOIDS; REGIOSELECTIVE SYNTHESIS; RH(II) CATALYST; CYCLIZATION; GENERATION; CASCADE;

D O I：

10.1021/ol2027625

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of enantioselective intermolecular cycloaddition of carbonyl ylides with indoles Is described. The cycloaddition of five- and six-membered carbonyl ylides derived from diazodiketoesters with N-methylindoles under catalysis by dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate), Rh-2(S-TCPTTL)(4), gave cycloadducts in high yields and with high levels of enantioselectivity (up to 99% ee) as well as excellent exo diastereoselectivity.

引用

页码：6284 / 6287

页数：4

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