Stereoselective double reduction of α,β-unsaturated imines

Overview

Many natural and biologically active compounds feature at least one amine function, often accompanied by multiple asymmetric centers. While numerous methodologies have been developed to synthesize these chiral amines, existing approaches suffer from significant limitations: they are either sequential with poor diastereoselectivity control, restricted to producing a single stereoisomer, or capable of controlling only one asymmetric center at a time.This project aims to address these challenges by achieving the

fully controlled, stereoselective double hydrogenation of

α

β

-unsaturated imines

using dual catalysis. A key advantage of this methodology is its ability to simultaneously control

up to three asymmetric centers

in a

stereodivergent manner . While chemoselective reductions of either imine groups or C=C double bonds in α,β-unsaturated ketones have been explored by other research groups,

no precedent exists for the proposed double reduction of

α

β

-unsaturated imines . The success of this project hinges on the synergistic use of

two distinct catalysts : one specialized for reducing the double bond and another for imine reduction. This interdisciplinary effort will be made possible through a collaboration between the

SERCO team at DCM , experts in organic synthesis, and the

PMB team at LCBM , specialists in the synthesis and characterization of organometallic complexes. Ultimately, this innovative methodology will enable the synthesis of

optically active amines

with biological relevance by controlling all newly formed asymmetric centers through the development of chemoselective catalysts. Topic description

Many natural and biologically active compounds feature at least one amine function, often accompanied by multiple asymmetric centers. While numerous methodologies have been developed to synthesize these chiral amines, existing approaches suffer from significant limitations: they are either sequential with poor diastereoselectivity control, restricted to producing a single stereoisomer, or capable of controlling only one asymmetric center at a time.This project aims to address these challenges by achieving the

fully controlled, stereoselective double hydrogenation of

α

β

-unsaturated imines

using dual catalysis. A key advantage of this methodology is its ability to simultaneously control

up to three asymmetric centers

in a

stereodivergent manner . While chemoselective reductions of either imine groups or C=C double bonds in α,β-unsaturated ketones have been explored by other research groups,

no precedent exists for the proposed double reduction of

α

β

-unsaturated imines . The success of this project hinges on the synergistic use of

two distinct catalysts : one specialized for reducing the double bond and another for imine reduction. This interdisciplinary effort will be made possible through a collaboration between the

SERCO team at DCM , experts in organic synthesis, and the

PMB team at LCBM , specialists in the synthesis and characterization of organometallic complexes. Ultimately, this innovative methodology will enable the synthesis of

optically active amines

with biological relevance by controlling all newly formed asymmetric centers through the development of chemoselective catalysts. Starting date -10-01

Funding category Other public funding

Funding further details Labex Arcane Stereoselective double reduction of unsaturated imines • , Auvergne-Rhône-Alpes, FR

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