Pd/Cu-Cocatalyzed Asymmetric Cascade Heck/Tsuji–Trost Reaction to Access Non-natural Tryptophans DOI
Panpan Li, Yang Zhang,

Zijiao Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 20, 2024

A Pd-catalyzed asymmetric Heck cascade reaction involving the intramolecular carbopalladation of unsaturated hydrocarbons, followed by nucleophilic trapping resulting palladium species, is a powerful approach for constructing chiral N-heterocycles. However, use prochiral nucleophiles in these reactions remains significantly underexplored. Herein, we report novel Pd/Cu catalytic system Heck/Tsuji–Trost allenamides and aldimine esters. This robust method allows rapid synthesis wide range enantiopure non-natural α-substituted tryptophans high yields (up to 99% yield) with excellent enantioselectivities 98% ee). Additionally, synthetic utility this protocol demonstrated through scale-up experiments diverse valuable transformations.

Language: Английский

Pd/Cu-Cocatalyzed Asymmetric Cascade Heck/Tsuji–Trost Reaction to Access Non-natural Tryptophans DOI
Panpan Li, Yang Zhang,

Zijiao Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 20, 2024

A Pd-catalyzed asymmetric Heck cascade reaction involving the intramolecular carbopalladation of unsaturated hydrocarbons, followed by nucleophilic trapping resulting palladium species, is a powerful approach for constructing chiral N-heterocycles. However, use prochiral nucleophiles in these reactions remains significantly underexplored. Herein, we report novel Pd/Cu catalytic system Heck/Tsuji–Trost allenamides and aldimine esters. This robust method allows rapid synthesis wide range enantiopure non-natural α-substituted tryptophans high yields (up to 99% yield) with excellent enantioselectivities 98% ee). Additionally, synthetic utility this protocol demonstrated through scale-up experiments diverse valuable transformations.

Language: Английский

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