Enantioselective\nCascade Catalysis for the Construction\nof Tetrahydroquinolines

Secondary amines are widely used as robust catalysts\nfor the enantioselective\nfunctionalization of aldehydes, yet they are rarely employed as Lewis\nbases or hydrogen-bonding catalysts for alkene activation. In this\nstudy, we present a decarboxylative [4 + 2] cycloaddition of vinyl\nbenzoxazinanones with nitroolefins to construct tetrahydroquinolines\nthrough cascade catalysis. A single chiral morpholine catalyst sequentially\nfunctions as both a Lewis base and a hydrogen-bonding catalyst. These\nactivation modes effectively drive the cascade process and control\nthe stereochemistry.

Publication Details

Journal
Figshare
Published
2024-10-30
DOI
https://doi.org/10.1021/acs.orglett.4c03311.s001
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
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article

Enantioselective\nCascade Catalysis for the Construction\nof Tetrahydroquinolines

Figshare
Asymmetric Synthesis and Catalysis
article

Enantioselective\nCascade Catalysis for the Construction\nof Tetrahydroquinolines

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Abstract

Secondary amines are widely used as robust catalysts\nfor the enantioselective\nfunctionalization of aldehydes, yet they are rarely employed as Lewis\nbases or hydrogen-bonding catalysts for alkene activation. In this\nstudy, we present a decarboxylative [4 + 2] cycloaddition of vinyl\nbenzoxazinanones with nitroolefins to construct tetrahydroquinolines\nthrough cascade catalysis. A single chiral morpholine catalyst sequentially\nfunctions as both a Lewis base and a hydrogen-bonding catalyst. These\nactivation modes effectively drive the cascade process and control\nthe stereochemistry.

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Asymmetric Synthesis and Catalysis
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Enantioselective\nCascade Catalysis for the Construction\nof Tetrahydroquinolines · Figshare (2024) | TGRS Research Map | TGRS