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Breaking the Symmetry of Axially Chiral N ‐Aryl‐2(1 H )‐pyrimidinones by Spontaneous Crystallization
Author(s) -
Sakamoto Masami,
Utsumi Noriyuki,
Ando Masaru,
Saeki Mizuho,
Mino Takashi,
Fujita Tsutomu,
Katoh Akira,
Nishio Takehiko,
Kashima Choji
Publication year - 2003
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.200351660
Subject(s) - crystallization , chirality (physics) , axial symmetry , chemistry , aryl , axial chirality , chiral symmetry breaking , combinatorial chemistry , organic chemistry , enantioselective synthesis , physics , symmetry breaking , catalysis , quantum mechanics , alkyl , nambu–jona lasinio model
No outside source of chirality was needed to resolve the racemate of an axially chiral pyrimidinone (see scheme). Crystallization at high temperatures gave optically active material in up to 73 % ee. The resolved product could be reduced with NaBH 4 with high enantioselectivity.