Mechanistic Insights of Copper Catalyzed Trifluoromethyl Aziridine Opening: Regioselective and Stereospecific Aryl Grignard Addition

The copper catalyzed regioselective and stereospecific opening of CF3-aziridines is reported. This method focuses on the synthesis of α-CF3-β-arylethylamines, which can be potential key intermediates in the synthesis of synthetic analogues and biologically active molecules. Density functional theory...

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Veröffentlicht in:	Organic letters 2024-04, Vol.26 (14), p.2713-2717
Hauptverfasser:	Lee, Miseon, Sulwey, Dennis, Rotella, Madeline E., Kim, Wan Shin, Ju, Xuan, Jiang, Qi, Kozlowski, Marisa C., Lee, Jaehee
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Sprache:	eng
Schlagworte:	copper density functional theory ethyleneimine Lewis acids regioselectivity stereospecificity
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container_title	Organic letters
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creator	Lee, Miseon Sulwey, Dennis Rotella, Madeline E. Kim, Wan Shin Ju, Xuan Jiang, Qi Kozlowski, Marisa C. Lee, Jaehee
description	The copper catalyzed regioselective and stereospecific opening of CF3-aziridines is reported. This method focuses on the synthesis of α-CF3-β-arylethylamines, which can be potential key intermediates in the synthesis of synthetic analogues and biologically active molecules. Density functional theory calculations reveal the nature of the active copper species and the role of the LiClMgX2 (X = Cl or I) as a Lewis acid. Further, the computed mechanism accounts for the high regioselectivity of this transformation.
doi_str_mv	10.1021/acs.orglett.3c01122
format	Article
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subjects	copper density functional theory ethyleneimine Lewis acids regioselectivity stereospecificity
title	Mechanistic Insights of Copper Catalyzed Trifluoromethyl Aziridine Opening: Regioselective and Stereospecific Aryl Grignard Addition
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