Enantioselective Construction of Tetrahydroindole Skeletons by Rh‐Catalyzed [2+2+2] Cycloaddition of Homopropargyl Enamides with Alkynes

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(38)

Published: June 26, 2024

We have developed the Rh-catalyzed enantioselective [2+2+2] cycloaddition of homopropargyl enamides (tosylamide-tethered 1,6-enynes) with alkynes to construct tetrahydroindole skeletons found in natural alkaloids and pharmaceuticals. This proceeds at room temperature high yields regio- enantioselectivity a broad substrate scope. The preparative scale reaction followed by substituent conversion on nitrogen atom diastereoselective [4+2] singlet O

Language: Английский

Enantioselective Construction of Tetrahydroindole Skeletons by Rh‐Catalyzed [2+2+2] Cycloaddition of Homopropargyl Enamides with Alkynes

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(38)

Published: June 26, 2024

Abstract We have developed the Rh‐catalyzed enantioselective [2+2+2] cycloaddition of homopropargyl enamides (tosylamide‐tethered 1,6‐enynes) with alkynes to construct tetrahydroindole skeletons found in natural alkaloids and pharmaceuticals. This proceeds at room temperature high yields regio‐ enantioselectivity a broad substrate scope. The preparative scale reaction followed by substituent conversion on nitrogen atom diastereoselective [4+2] singlet O 2 affords hexahydroindole‐diols bearing three stereogenic centers variable substituents nitrogen. Mechanistic studies revealed that enynes change ratio intramolecular intermolecular rhodacycle formation when using terminal alkynes, varying ee values cycloadducts.

Language: Английский