Organocatalytic Enantioselective alpha-Nitrogenation of alpha,alpha- Disubstituted Aldehydes in the Absence of a Solvent

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Date
2022-10
Author
Torregrosa Chinillach, Alejandro
Carral Menoyo, Asier
Gómez Bengoa, Enrique
Chinchilla Cruz, Rafael
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The Journal of Organic Chemistry 87(21) : 14507-14513 (2022)
URI
http://hdl.handle.net/10810/58544
Abstract
A highly efficient enantioselective alpha-nitrogenation method of alpha,alpha-disubstituted aldehydes with azodicarboxylates promoted by a chiral carbamate-monoprotected cyclohexa-1,2diamine as organocatalyst has been developed. The process was carried out without any solvent, and the corresponding alpha,alpha- disubstituted alpha-nitrogenated aldehydes were obtained with excellent yields and enantioselectivities up to 99% ee. The sustainability of the procedure was established through the calculation of green metrics, such as EcoScale and E-factor. In addition, theoretical calculations have been used to justify the obtained enantioselectivity sense.
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© 2022 The Authors. Published by American Chemical Society. Attribution 4.0 International (CC BY 4.0)
Except where otherwise noted, this item's license is described as © 2022 The Authors. Published by American Chemical Society. Attribution 4.0 International (CC BY 4.0)