Archives for Chemistry Experiments of 5430-45-5

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N-heterocyclic carbene catalyzed enantioselective [3 + 2] dearomatizing annulation of saturated carboxylic esters with n-iminoisoquinolinium ylides

The dearomatizing annulation reaction is a significant challenge in organic chemistry. The direct activation of alpha-carbons of simple saturated esters, as nucleophiles, is an important synthesis strategy. In the present study, we disclose [3 + 2] dearomatizing annulation reactions with direct activating alpha-carbons of saturated carboxylic esters and N-iminoisoquinolinium ylides, which possess highly enantioselective characteristics, catalyzed by N-heterocyclic carbenes (NHCs). The protocol achieves isoquinoline dearomatization and the construction of tricyclic chiral products under mild conditions with good yield, substrate tolerance, and diastereoselectivity as well as excellent enantioselectivity.

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Reference：
Isoquinoline – Wikipedia,
Isoquinoline | C9H1564N – PubChem