Iodomethylation of Chiral α-Amino Aldehydes by Means of Samarium/Diiodomethane. Application to the Synthesis of Various Enantiomerically Pure Compounds

1997 ◽  
Vol 62 (25) ◽  
pp. 8902-8906 ◽  
Author(s):  
José M. Concellón ◽  
Pablo L. Bernad ◽  
Juan A. Pérez-Andrés
Keyword(s):  
Enantiomerically Pure ◽  
Amino Aldehydes ◽  
Pure Compounds

scholarly journals Altering the Stereoselectivity of Whole-Cell Biotransformations via the Physicochemical Parameters Impacting the Processes

Catalysts ◽  
2021 ◽  
Vol 11 (7) ◽  
pp. 781
Author(s):  
Agnieszka Raczyńska ◽  
Joanna Jadczyk ◽  
Małgorzata Brzezińska-Rodak
Keyword(s):  
Culture Conditions ◽  
Biologically Active ◽  
Enantiomerically Pure ◽  
Whole Cells ◽  
Chiral Compounds ◽  
Physicochemical Factors ◽  
Pure Compounds ◽  
Genetic Level ◽  
Prochiral Ketones ◽  
Optically Pure

The enantioselective synthesis of organic compounds is one of the great challenges in organic synthetic chemistry due to its importance for the acquisition of biologically active derivatives, e.g., pharmaceuticals, agrochemicals, and others. This is why biological systems are increasingly applied as tools for chiral compounds synthesis or modification. The use of whole cells of “wild-type” microorganisms is one possible approach, especially as some methods allow improving the conversion degrees and controlling the stereoselectivity of the reaction without the need to introduce changes at the genetic level. Simple manipulation of the culture conditions, the form of a biocatalyst, or the appropriate composition of the biotransformation medium makes it possible to obtain optically pure products in a cheap, safe, and environmentally friendly manner. This review contains selected examples of the influence of physicochemical factors on the stereochemistry of the biocatalytic preparation of enantiomerically pure compounds, which is undertaken through kinetically controlled separation of their racemic mixtures or reduction of prochiral ketones and has an effect on the final enantiomeric purity and enantioselectivity of the reaction.

scholarly journals Asymmetric Mannich reactions of (S)-N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines with yne nucleophiles

2020 ◽  
Vol 16 ◽  
pp. 2671-2678
Author(s):  
Ziyi Li ◽  
Li Wang ◽  
Yunqi Huang ◽  
Haibo Mei ◽  
Hiroyuki Konno ◽  
...  
Keyword(s):  
Column Chromatography ◽  
Addition Reactions ◽  
Mannich Reactions ◽  
Enantiomerically Pure ◽  
Pure Compounds

In the present work, arylethynes were studied as new C-nucleophiles in the asymmetric Mannich addition reactions with (S)-N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimine. The reactions were conducted under operationally convenient conditions affording the corresponding Mannich adducts with up to 87% yield and 70:30 diastereoselectivity. The isomeric products can be separated using regular column chromatography to afford diastereomerically pure compounds. The purified Mannich addition products were deprotected to give the target enantiomerically pure trifluoromethylpropargylamines. A mechanistic rationale for the observed stereochemical outcome is discussed.

ChemInform Abstract: Hydrolases in Organic Synthesis: Preparation of Enantiomerically Pure Compounds

ChemInform ◽  
2010 ◽  
Vol 23 (43) ◽  
pp. no-no
Author(s):  
U. ADER ◽  
P. ANDERSCH ◽  
M. BERGER ◽  
U. GOERGENS ◽  
R. SEEMAYER ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Enantiomerically Pure ◽  
Pure Compounds

ChemInform Abstract: Enantiomerically Pure α-Amino Aldehydes from Silylated α-Amino Acids.

ChemInform ◽  
2008 ◽  
Vol 39 (26) ◽  
Author(s):  
Buddy Soto-Cairoli ◽  
Jorge Justo de Pomar ◽  
John A. Soderquist
Keyword(s):  
Amino Acids ◽  
Enantiomerically Pure ◽  
Amino Aldehydes
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