西亚试剂：Direct Alkenylation of Indoles with α-Oxo Ketene Dithioacet

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

Haifeng Yu, Dr. 1, Zhengkun Yu, Prof. Dr. 1 2 *

1Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023 (P.R. China), Fax: (+86) 411-8437-9227,2State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (P.R. China)

*Correspondence to Zhengkun Yu, 1Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023 (P.R. China)

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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