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

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The first enantioselective and diastereoselective synthesis of atropisomeric hydrazides was performed using one-pot sequential catalysis based on the enamine amination of branched aldehydes followed by phase-transfer N-alkylation. Chiral hydrazides were obtained with high yields and stereocontrol using commercially available reagents and catalysts. The permutation of catalysts allowed for a stereodivergent approach to a new class of atropisomers.


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.

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