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Journal Article
Research Support, Non-U.S. Gov't
An Arylation Strategy to Propargylamines: Catalytic Asymmetric Friedel-Crafts-type Arylation Reactions of C-Alkynyl Imines.
Angewandte Chemie 2016 November 22
The first arylation strategy for the synthesis of enantioenriched propargylamines is disclosed. This approach, which is complementary to previous alkynylation and alkylation strategies, involves a C(sp2 )-C(sp3 ) bond formation, and is based on the first asymmetric Friedel-Crafts-type arylation reaction of C-alkynyl imines. Asymmetric Friedel-Crafts reactions with electron-deficient phenols, a longstanding unsolved challenge, have thus been realized for the first time, enabled by the combination of our recently introduced C-alkynyl N-Boc-protected N,O-acetals as electrophiles and chiral phosphoric acids as catalysts. The synthetic utility of the resulting structurally diverse and polyfunctional chiral propargylamines was demonstrated by a series of selective transformations, including controlled reduction of the alkynyl group and iterative cross-couplings.
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