首页|Conformationally locked cis-1,2-diaminocyclohexane-based chiral ligands for asymmetric catalysis

Conformationally locked cis-1,2-diaminocyclohexane-based chiral ligands for asymmetric catalysis

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An efficient synthesis for a new conformationally locked chiral cis-1,2-diaminocyclohexane scaffold has been developed. The conformational lock allows for convenient symmetrical derivatization of the amino groups through the reductive amination strategy. A series of optically pure chiral ligands based on the cis-DACH scaffold has been generated to demonstrate a proof-of-concept for these ligands as chiral catalysts in the asymmetric Henry reaction. Excellent yields with moderate enantioselectivity were demonstrated at room temperature, with an increase in enantioselectivity at lower temperatures, showing the potential of this new type of cis-DACH ligand.(c) 2022 Elsevier Ltd. All rights reserved.

Chiralcis-12-diaminocyclohexanesChiral cis-DACH ligandsConformational lockChemical resolutionEnzymatic resolutionAsymmetric Henry ReactionHENRY REACTIONTRANSFER HYDROGENATIONDIAMINESKETONES

van Beek, Carim、Samoshin, Vyacheslav V.

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Univ Pacific

2022

Tetrahedron letters

Tetrahedron letters

CCR
ISSN:0040-4039
年,卷(期):2022.102
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