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Chiral Calcium Iodide for Asymmetric Mannich‐type Reactions of Malonates with Imines Providing β‐Aminocarbonyl Compounds
Author(s) -
Tsubogo Tetsu,
Shimizu Shota,
Kobayashi Shū
Publication year - 2013
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201300102
Subject(s) - chemistry , enantioselective synthesis , adduct , catalysis , iodide , combinatorial chemistry , organic chemistry , mannich reaction
Out of the pybox : We have developed a novel chiral calcium iodide catalyst from CaI 2 and a pybox that is stable under moisture and oxygen. This catalyst was applied to catalytic asymmetric Mannich‐type reactions of malonates with both N ‐Boc‐protected aromatic and aliphatic imines, and resulted in moderate to high yields with high enantioselectivities. To the best of our knowledge, this is the first example of highly enantioselective metal‐catalyzed asymmetric Mannich‐type reactions of malonates with N ‐Boc‐protected aliphatic imines. The Mannich adduct was successfully converted into the α‐hydroxy β‐amino acid derivative. We have also shown the unique structure of the chiral Ca complexes with malonates.