Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 42, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202209895
Keywords
Diastereoselectivity; Enantioselectivity; N-N Atropisomers; Organocatalysis; Phase-Transfer Catalysis
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Funding
- University of Bologna
- Consorzio Interuniversitario Nazionale per la Scienza e Tecnologia dei Materiali (INSTM)
- Universita degli Studi di Bologna within the CRUI-CARE Agreement
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The first catalytic enantioselective and diastereoselective synthesis of atropisomeric hydrazides was achieved using a sequential catalysis protocol, providing a stereodivergent approach to enantioenriched atropisomeric hydrazides. The resulting axially chiral hydrazides were obtained directly from commercially available reagents in high yields and with good stereocontrol, demonstrating the effectiveness of this strategy.
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.
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