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

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

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-l...

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Veröffentlicht in:Organic letters 2011-12, Vol.13 (23), p.6284-6287
Hauptverfasser: Shimada, Naoyuki, Oohara, Tadashi, Krishnamurthi, Janagiraman, Nambu, Hisanori, Hashimoto, Shunichi
Format: Artikel
Sprache:eng
Schlagworte:
Azo Compounds - chemistry
Carboxylic Acids - chemistry
Catalysis
Cyclization
Indoles - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Rhodium - chemistry
Stereoisomerism
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Zusammenfassung: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], Rh2(S-TCPTTL)4, gave cycloadducts in high yields and with high levels of enantioselectivity (up to 99% ee) as well as excellent exo diastereoselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2027625