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Abstract | Cited by

A new organocatalytic quadruple domino Friedel–Crafts-type/Michael/Michael/aldol condensation reaction has been developed. In this one-pot multi-component process acrolein, various indoles and nitroalkenes are used as starting materials. The diphenylprolinol TMS-ether catalysis provides a straightforward and efficient entry to 3-(cyclohexenylmethyl)-indoles bearing three stereogenic centers in moderate to excellent yields (23–82%) and excellent stereoselectivities (dr = 91 ∶ 9 to >95 ∶ 5, ee = 94 to >99%).

Graphical abstract: Organocatalytic asymmetric synthesis of polyfunctionalized 3-(cyclohexenylmethyl)-indoles via a quadruple domino Friedel–Crafts-type/Michael/Michael/aldol condensation reaction

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