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Which Is the Actual Catalyst: Chiral Phosphoric Acid or Chiral Calcium Phosphate?
Author(s) -
Hatano Manabu,
Moriyama Katsuhiko,
Maki Toshikatsu,
Ishihara Kazuaki
Publication year - 2010
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.201000824
Subject(s) - phosphoric acid , catalysis , enantioselective synthesis , aldimine , chemistry , stereoselectivity , phosphate , organic chemistry , organocatalysis , calcium
Both catalysts work : A highly enantioselective direct Mannich‐type reaction of N ‐Boc‐protected aldimines with 1,3‐dicarbonyl compounds has been developed with the use of a chiral phosphoric acid in the presence or absence of Ca II . The absolute stereoselectivity of the phosphoric acid catalysis was found to be opposite to that of the calcium phosphate catalysis (see scheme; Boc= tert ‐butoxycarbonyl).
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