Maxime Giardinetti, Xavier Moreau, Vincent Coeffard
Nov 16, 2015
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Journal
Advanced Synthesis & Catalysis
Abstract
We report herein a new cascade strategy for the enantioselective synthesis of 1,7-annulated indoles based on iminium-enamine activation. A careful study of the indole substitution pattern revealed that a chloro substituent at the C-3 position was important to the implementation of the reaction. Employing a diphenylprolinol silyl ether catalyst, a range of 3-chloro-1H-indole-7-carbaldehyde derivatives reacted with α,β-unsaturated aldehydes to afford the corresponding 1,7-annulated indoles in good yields (62–99%) and enantioselectivities (62–92%). Besides the fluorescence properties of the 1,7-ring fused indoles prepared following our methodology, these compounds contain a useful set of functional groups which undergo various synthetic transformations.