Enantioselective Conjugate Azidation of α,β ‐Unsaturated Ketones under Bifunctional Organocatalysis by Direct Activation of TMSN 3
An enantioselective organocatalytic conjugate azidation of α,β‐unsaturated ketones is presented. A bifunctional organocatalyst activates TMSN 3 , triggering the nucleophilic addition of the azido group to enones in absence of external promoters and avoiding the direct use or the pre‐formation of hig...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2019-10, Vol.361 (20), p.4790-4796 |
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| container_title | Advanced synthesis & catalysis |
| container_volume | 361 |
| creator | Humbrías‐Martín, Jorge Pérez‐Aguilar, M. Carmen Mas‐Ballesté, Rubén Dentoni Litta, Antonella Lattanzi, Alessandra Della Sala, Giorgio Fernández‐Salas, Jose A. Alemán, José |
| description | An enantioselective organocatalytic conjugate azidation of α,β‐unsaturated ketones is presented. A bifunctional organocatalyst activates TMSN
3
, triggering the nucleophilic addition of the azido group to enones in absence of external promoters and avoiding the direct use or the pre‐formation of highly toxic and explosive hydrazoic acid. This protocol proceeds with excellent enantiocontrol under mild conditions. DFT calculations and mechanistic trials have been performed in order to demonstrate the direct activation performed by the bifunctional organocatalyst.
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| doi_str_mv | 10.1002/adsc.201900831 |
| format | Article |
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3
, triggering the nucleophilic addition of the azido group to enones in absence of external promoters and avoiding the direct use or the pre‐formation of highly toxic and explosive hydrazoic acid. This protocol proceeds with excellent enantiocontrol under mild conditions. DFT calculations and mechanistic trials have been performed in order to demonstrate the direct activation performed by the bifunctional organocatalyst.
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, triggering the nucleophilic addition of the azido group to enones in absence of external promoters and avoiding the direct use or the pre‐formation of highly toxic and explosive hydrazoic acid. This protocol proceeds with excellent enantiocontrol under mild conditions. DFT calculations and mechanistic trials have been performed in order to demonstrate the direct activation performed by the bifunctional organocatalyst.
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3
, triggering the nucleophilic addition of the azido group to enones in absence of external promoters and avoiding the direct use or the pre‐formation of highly toxic and explosive hydrazoic acid. This protocol proceeds with excellent enantiocontrol under mild conditions. DFT calculations and mechanistic trials have been performed in order to demonstrate the direct activation performed by the bifunctional organocatalyst.
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| source | Wiley Online Library - AutoHoldings Journals |
| title | Enantioselective Conjugate Azidation of α,β ‐Unsaturated Ketones under Bifunctional Organocatalysis by Direct Activation of TMSN 3 |
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