The first catalytic enantioselective and diastereoselective synthesis of atropisomeric hydrazides was achieved using a sequential catalysis protocol. This strategy is based on a one-pot sequence of two organocatalytic cycles featuring the enamine amination of branched aldehydes followed by nitrogen alkylation under phase-transfer conditions. The resulting axially chiral hydrazides were obtained directly from commercially available reagents in high yields and with good stereocontrol. The permutation of organocatalysts allowed easy access to all stereoisomers, enabling a stereodivergent approach to enantioenriched atropisomeric hydrazides.

Synthesis of Atropisomeric Hydrazides by One‐Pot Sequential Enantio‐ and Diastereoselective Catalysis / Portolani, Chiara; Centonze, Giovanni; Luciani, Sara; Pellegrini, Andrea; Righi, Paolo; Mazzanti, Andrea; Ciogli, Alessia; Sorato, Andrea; Bencivenni, Giorgio. - In: ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. - ISSN 1433-7851. - (2022). [10.1002/anie.202209895]

Synthesis of Atropisomeric Hydrazides by One‐Pot Sequential Enantio‐ and Diastereoselective Catalysis

Alessia Ciogli;Andrea Sorato;
2022

Abstract

The first catalytic enantioselective and diastereoselective synthesis of atropisomeric hydrazides was achieved using a sequential catalysis protocol. This strategy is based on a one-pot sequence of two organocatalytic cycles featuring the enamine amination of branched aldehydes followed by nitrogen alkylation under phase-transfer conditions. The resulting axially chiral hydrazides were obtained directly from commercially available reagents in high yields and with good stereocontrol. The permutation of organocatalysts allowed easy access to all stereoisomers, enabling a stereodivergent approach to enantioenriched atropisomeric hydrazides.
2022
Diastereoselectivity; Enantioselectivity; N−N Atropisomers; Organocatalysis; Phase-Transfer Catalysis
01 Pubblicazione su rivista::01a Articolo in rivista
Synthesis of Atropisomeric Hydrazides by One‐Pot Sequential Enantio‐ and Diastereoselective Catalysis / Portolani, Chiara; Centonze, Giovanni; Luciani, Sara; Pellegrini, Andrea; Righi, Paolo; Mazzanti, Andrea; Ciogli, Alessia; Sorato, Andrea; Bencivenni, Giorgio. - In: ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. - ISSN 1433-7851. - (2022). [10.1002/anie.202209895]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1654159
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