893404-25-6Relevant academic research and scientific papers
Hydrogen-bond-directed enantioselective decarboxylative mannich reaction of β-ketoacids with ketimines: Application to the synthesis of anti-HIV drug DPC 083
Yuan, Hai-Na,Wang, Shuai,Nie, Jing,Meng, Wei,Yao, Qingwei,Ma, Jun-An
supporting information, p. 3869 - 3873 (2013/05/08)
Key to success: The title reaction provides facile access to enantioenriched 3,4-dihydroquinazolin-2(1H)-ones containing a quaternary stereogenic center in high yields with excellent enantioselectivities. Subsequent transformations lead to the convenient preparation of the anti-HIV drug DPC 083 and N-fused polycyclic compounds without loss of enantiomeric excess.
Highly enantioselective construction of a quaternary carbon center of dihydroquinazoline by asymmetric Mannich reaction and chiral recognition
Jiang, Biao,Jia, Jia Dong,Yu, Gui Si,Xiao, Long Zhao,Zuo, Gang Huang,Xu, Min
scheme or table, p. 1360 - 1366 (2009/06/05)
The highly enantioselective construction of a quaternary carbon center of dihydroquinazoline by an asymmetric Mannich reaction and chiral recognition are described. The key transformation was to establish the chiral trifluoromethyl quaternary carbon center bya diamine-Bronsted acid-catalyzed enantioselective and regioselective Mannich reaction of a methyl ketone and 4-trifluoromethyldihydroquinazoline. An unusual phenomenon of self-discrimination of enantiomers in hydrogen-bonded dimers was observed. A valuable intermediate was transformed into the enantiopure HIV reverse transcriptase inhibitor DPC 083 (>99.9 ee) simplyby reduction of the carbonyl group and elimination of the hydroxy group in hexamethylphosphoric tramide (HMPA).
