Synthesis of bridgehead-azacycles via dual C–N/C–C annulation of α-amino acids, aminals and maleimides

The synthesis of various bridged azacyclic adducts has recently become a reemerging topic due to their bioactive and natural product mimic profiles. Accordingly, herein, we report a method for easy access to succinamide-bridged azacyclic derivatives through the metal-free polarization-controlled dua...

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Veröffentlicht in:	Organic & biomolecular chemistry 2022-08, Vol.20 (32), p.6368-6383
Hauptverfasser:	Thadem, Nagender, Rajesh, Manda, Balaboina, Harikrishna, Das, Saibal
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Sprache:	eng
Schlagworte:	Adducts Aldehydes Amino acids Chemical reactions Cycloaddition Natural products Organic chemistry Substrates Succinamide Synthesis
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container_title	Organic & biomolecular chemistry
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creator	Thadem, Nagender Rajesh, Manda Balaboina, Harikrishna Das, Saibal
description	The synthesis of various bridged azacyclic adducts has recently become a reemerging topic due to their bioactive and natural product mimic profiles. Accordingly, herein, we report a method for easy access to succinamide-bridged azacyclic derivatives through the metal-free polarization-controlled dual C–N/C–C annulation of readily available α-amino acids, 2-amino benzaldehydes or pyrrole/indole-2-aldehyde and maleimide substrates. This cascade features a rare dipolarophile-induced diastereo-selective amidative annulation, followed by 3 + 2 cycloaddition as key steps.
doi_str_mv	10.1039/d2ob01117d
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subjects	Adducts Aldehydes Amino acids Chemical reactions Cycloaddition Natural products Organic chemistry Substrates Succinamide Synthesis
title	Synthesis of bridgehead-azacycles via dual C–N/C–C annulation of α-amino acids, aminals and maleimides
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