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Catalytic Asymmetric Synthesis of Dihydroquinazolinones from Imines and 2‐Aminobenzamides
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AbstractAn unprecedented catalytic asymmetric synthesis of aminal‐containing heterocyclic compounds has been developed from imines and tethered nitrogen/nitrogen nucleophiles. In the presence of 10 mol% of a commercially available chiral phosphoric acid, a range of aromatic, α,β‐unsaturated, and aliphatic imines react with 2‐aminobenzamides to give dihydroquinazolinones in good to excellent yields and ee. The enantioselectivity is significantly affected by the imine N‐substituent through non‐bonding interactions with the chiral phosphoric acid and the 2‐aminobenzamide.
Title: Catalytic Asymmetric Synthesis of Dihydroquinazolinones from Imines and 2‐Aminobenzamides
Description:
AbstractAn unprecedented catalytic asymmetric synthesis of aminal‐containing heterocyclic compounds has been developed from imines and tethered nitrogen/nitrogen nucleophiles.
In the presence of 10 mol% of a commercially available chiral phosphoric acid, a range of aromatic, α,β‐unsaturated, and aliphatic imines react with 2‐aminobenzamides to give dihydroquinazolinones in good to excellent yields and ee.
The enantioselectivity is significantly affected by the imine N‐substituent through non‐bonding interactions with the chiral phosphoric acid and the 2‐aminobenzamide.
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