Highly Enantioselective Iridium-Catalyzed Coupling Reaction of Vinyl Azides and Racemic Allylic Carbonates

Highly Enantioselective Iridium-Catalyzed Coupling Reaction of Vinyl Azides and Racemic Allylic Carbonates

The iridium-catalyzed enantioselective coupling reaction of vinyl azides and allylic electrophiles is presented and provides access to β-chiral carbonyl derivatives. Vinyl azides are used as acetamide enolate or acetonitrile carbanion surrogates, leading to γ,δ-unsaturated β-substituted amides as we...

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Veröffentlicht in:Journal of the American Chemical Society 2020-08, Vol.142 (31), p.13398-13405
Hauptverfasser: Han, Min, Yang, Min, Wu, Rui, Li, Yang, Jia, Tao, Gao, Yuanji, Ni, Hai-Liang, Hu, Ping, Wang, Bi-Qin, Cao, Peng
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container_end_page 13405
container_issue 31
container_start_page 13398
container_title Journal of the American Chemical Society
container_volume 142
creator Han, Min
Yang, Min
Wu, Rui
Li, Yang
Jia, Tao
Gao, Yuanji
Ni, Hai-Liang
Hu, Ping
Wang, Bi-Qin
Cao, Peng
description The iridium-catalyzed enantioselective coupling reaction of vinyl azides and allylic electrophiles is presented and provides access to β-chiral carbonyl derivatives. Vinyl azides are used as acetamide enolate or acetonitrile carbanion surrogates, leading to γ,δ-unsaturated β-substituted amides as well as nitriles with excellent enantiomeric excess. These products are readily transformed into chiral N-containing building blocks and pharmaceuticals. A mechanism is proposed to rationalize the chemoselectivity of this coupling reaction.
doi_str_mv 10.1021/jacs.0c01766
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title Highly Enantioselective Iridium-Catalyzed Coupling Reaction of Vinyl Azides and Racemic Allylic Carbonates
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