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Catalytic Asymmetric Synthesis of Dihydroquinazolinones from Imines and 2‐Aminobenzamides
Author(s) -
Cheng DaoJuan,
Tian Yu,
Tian ShiKai
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100849
Subject(s) - chemistry , imine , aminal , substituent , catalysis , phosphoric acid , nucleophile , enantioselective synthesis , organic chemistry , organocatalysis , nitrogen , combinatorial chemistry
An 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.