Diastereoselective Mannich reactions of pseudo-C 2-symmetric glutarimide with activated imines

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.13.244 ◽

2017 ◽

Vol 13 ◽

pp. 2473-2477 ◽

Cited By ~ 1

Author(s):

Tatsuya Ishikawa ◽

Tomoko Kawasaki-Takasuka ◽

Toshio Kubota ◽

Takashi Yamazaki

Keyword(s):

Glutaric Acid ◽

Aldol Reactions ◽

Mannich Reactions

As an extension of the boron enolate-based aldol reactions, the oxazolidinone-installed bisimide 1a from 3-(trifluoromethyl)glutaric acid was employed for Mannich reactions with tosylated imines 2 as electrophiles to successfully obtain the corresponding adducts in a stereoselective manner.

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ChemInform Abstract: A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric anti-Selective Mannich Reactions and syn-Selective Cross-Aldol Reactions.

ChemInform ◽

10.1002/chin.200946067 ◽

2009 ◽

Vol 40 (46) ◽

Author(s):

Taichi Kano ◽

Yukako Yamaguchi ◽

Keiji Maruoka

Keyword(s):

Aldol Reactions ◽

Mannich Reactions ◽

Axially Chiral

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A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetricanti-Selective Mannich Reactions andsyn-Selective Cross-Aldol Reactions

Chemistry - A European Journal ◽

10.1002/chem.200900267 ◽

2009 ◽

Vol 15 (27) ◽

pp. 6678-6687 ◽

Cited By ~ 93

Author(s):

Taichi Kano ◽

Yukako Yamaguchi ◽

Keiji Maruoka

Keyword(s):

Aldol Reactions ◽

Mannich Reactions ◽

Axially Chiral

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Asymmetric Aldol Reactions, Mannich Reactions, and Michael Additions

Asymmetric Organocatalysis 2 ◽

10.1055/sos-sd-205-00614 ◽

2012 ◽

pp. 1

Author(s):

K. Izawa ◽

T. Torii ◽

T. Nishikawa ◽

H. Imai

Keyword(s):

Aldol Reactions ◽

Mannich Reactions ◽

Asymmetric Aldol ◽

Michael Additions

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Characterization of Chemical Impurities in Glutaraldehyde

Proceedings, annual meeting, Electron Microscopy Society of America ◽

10.1017/s0424820100116723 ◽

1975 ◽

Vol 33 ◽

pp. 620-621

Author(s):

B. J. Grenon ◽

A. J. Tousimis

Keyword(s):

Glutaric Acid ◽

Spectroscopic Analysis ◽

Aldol Condensation ◽

Condensation Product ◽

Amorphous Solid ◽

Water Soluble ◽

Impurity Component ◽

Chemical Impurities ◽

Soluble Liquid

Ever since the introduction of glutaraldehyde as a fixative in electron microscopy of biological specimens, the identification of impurities and consequently their effects on biologic ultrastructure have been under investigation. Several reports postulate that the impurities of glutaraldehyde, used as a fixative, are glutaric acid, glutaraldehyde polymer, acrolein and glutaraldoxime.Analysis of commercially available biological or technical grade glutaraldehyde revealed two major impurity components, none of which has been reported. The first compound is a colorless, water-soluble liquid with a boiling point of 42°C at 16 mm. Utilizing Nuclear Magnetic Resonance (NMR) spectroscopic analysis, this compound has been identified to be — dihydro-2-ethoxy 2H-pyran. This impurity component of the glutaraldehyde biological or technical grades has an UV absorption peak at 235nm. The second compound is a white amorphous solid which is insoluble in water and has a melting point of 80-82°C. Initial chemical analysis indicates that this compound is an aldol condensation product(s) of glutaraldehyde.

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