Direct Alkenylation of Indoles with α‐Oxo Ketene Dithioacetals: Efficient Synthesis of Indole Alkaloids Meridianin Derivatives | Zendy

Yu Haifeng | Zendy; Yu Zhengkun | Zendy

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Direct Alkenylation of Indoles with α‐Oxo Ketene Dithioacetals: Efficient Synthesis of Indole Alkaloids Meridianin Derivatives

Author(s) -

Yu Haifeng,

Yu Zhengkun

Publication year - 2009

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200900278

Subject(s) - ketene , trifluoroacetic acid , chemistry , indole test , guanidine , dichloromethane , condensation , organic chemistry , medicinal chemistry , physics , solvent , thermodynamics

Let's make 'meri' : Metal‐free direct alkenylation of indoles was realized by acid‐mediated substitution reactions of α‐oxo ketene dithioacetals with indoles in trifluoroacetic acid/dichloromethane, selectively affording β‐indolyl mono‐ and disubstituted α,β‐unsaturated carbonyl compounds (see scheme). Condensation of the indolyl/ketene monothioacetals and guanidine nitrate efficiently produced meridianin derivatives.

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