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Chiral Calcium Iodide for Asymmetric Mannich-type Reactions of Malonates With Imines Providing β-aminocarbonyl Compounds

Chiral Calcium Iodide for Asymmetric Mannich-type Reactions of Malonates With Imines Providing β-aminocarbonyl Compounds

Tetsu Tsubogo, Shota Shimizu, Shū Kobayashi

Chem Asian J. 2013 May;8(5):872-6.

PMID: 23494940

Abstract:

Out of the pybox: We have developed a novel chiral calcium iodide catalyst from CaI2 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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP10102688	Calcium iodide		10102-68-8	Price

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