A Titanium(III)-Catalyzed Reductive Umpolung Reaction for the Synthesis of 1,1-Disubstituted Tetrahydroisoquinolines

Organic Letters(2015)

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Abstract
A catalytic reductive C1-acylation of 3,4-dihydroisoquinolines is presented that gives direct access to 1,1-disubstituted tetrahydroisoquinolines. The reaction is a titanium­(III)-catalyzed reductive umpolung process in which nitriles act as effective acylation agents. The method is highly chemo- and regioselective and is demonstrated in 20 examples. It is well-suited for the large-scale synthesis of functionalized tetra­hydro­isoquinoline products, which is exemplified in the form of a six-step synthesis of (±)-3-demethoxy­erythratidinone.
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Key words
reductive umpolung reaction,synthesis,titaniumiii-catalyzed
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