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Hydrogen‐Bond‐Directed Enantioselective Decarboxylative Mannich Reaction of β‐Ketoacids with Ketimines: Application to the Synthesis of Anti‐HIV Drug DPC 083
Author(s) -
Yuan HaiNa,
Wang Shuai,
Nie Jing,
Meng Wei,
Yao Qingwei,
Ma JunAn
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201210361
Subject(s) - stereocenter , enantioselective synthesis , combinatorial chemistry , chemistry , human immunodeficiency virus (hiv) , enantiomer , computer science , medicinal chemistry , organic chemistry , catalysis , medicine , virology
Key to success : The title reaction provides facile access to enantioenriched 3,4‐dihydroquinazolin‐2(1 H )‐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.