Optically active amines. XVII. Partial kinetic resolution of .alpha.-phenylbutyric acid using chiral primary amines and their salts

1974 ◽  
Vol 39 (15) ◽  
pp. 2309-2311 ◽  
Author(s):  
Howard E. Smith ◽  
Annette Waters Gordon ◽  
Alec F. Bridges
Keyword(s):  
Kinetic Resolution ◽  
Optically Active ◽  
Primary Amines ◽  
Phenylbutyric Acid

Regioselectivity and stereoselectivity in the reaction of cis-1,2,2-Trimethylcyclopentane-1,3-dicarboxylic anhydride (cis-camphoric anhydride) with chiral primary amines

1981 ◽  
Vol 34 (3) ◽  
pp. 665 ◽  
Author(s):  
KH Bell
Keyword(s):  
Carbonyl Group ◽  
Absolute Configuration ◽  
Kinetic Resolution ◽  
Optically Active ◽  
Primary Amines ◽  
The Absolute

The reaction between primary amines and cis-1,2,2 trimethylcyclopentane-1,3-dicarboxylic anhydride (3) has been shown to be regioselective for the less hindered carbonyl group. Kinetic resolution was observed when racemic primary amines and the (1R,3S) anhydride (3) were used. Similar stereoselectivity was found in the alternative reaction between racemic (3) and optically active primary amines. In both cases, the absolute configuration of the more reactive enantiomeric amine or anhydride could be correlated with a model (7). The use of (3) is recommended for the prediction of the absolute configurations of racemic and optically active primary amines.

Kinetic resolution of N-methyl-2-phenylpyrrolidine by cyclopalladation in the presence of an optically active base

1999 ◽  
Vol 35 (8) ◽  
pp. 1001-1011 ◽  
Author(s):  
V. V. Dunina ◽  
L. G. Kuz'mina ◽  
E. D. Razmyslova ◽  
V. P. Kislyi
Keyword(s):  
Kinetic Resolution ◽  
Optically Active ◽  
Active Base

One-Pot Synthesis of Optically Active Cyanohydrin Acetates from Aldehydes via Quinidine-Catalyzed Transhydrocyanation Coupled with Lipase-Catalyzed Kinetic Resolution in Organic Solvent

1992 ◽  
Vol 65 (1) ◽  
pp. 111-120 ◽  
Author(s):  
Minoru Inagaki ◽  
Akihiko Hatanaka ◽  
Mitsuo Mimura ◽  
Jun Hiratake ◽  
Takaaki Nishioka ◽  
...  
Keyword(s):  
Organic Solvent ◽  
Kinetic Resolution ◽  
Optically Active ◽  
One Pot ◽  
One Pot Synthesis

scholarly journals Enantioselective Transfer Aminoallylation: Synthesis of Optically Active Homoallylic Primary Amines.

ChemInform ◽  
2007 ◽  
Vol 38 (1) ◽  
Author(s):  
Masaharu Sugiura ◽  
Chieko Mori ◽  
Shu Kobayashi
Keyword(s):  
Optically Active ◽  
Primary Amines

Optically Active Amines by Enzyme-Catalyzed Kinetic Resolution

Synthesis ◽  
2008 ◽  
Vol 2008 (14) ◽  
pp. 2283-2287 ◽  
Author(s):  
Klaus Ditrich
Keyword(s):  
Kinetic Resolution ◽  
Optically Active

ChemInform Abstract: Chemoenzymatic Dynamic Kinetic Resolution of Primary Amines Using a Recyclable Palladium Nanoparticle Catalyst Together with Lipases.

ChemInform ◽  
2014 ◽  
Vol 45 (38) ◽  
pp. no-no
Author(s):  
Karl P. J. Gustafson ◽  
Richard Lihammar ◽  
Oscar Verho ◽  
Karin Engstroem ◽  
Jan-E. Baeckvall
Keyword(s):  
Kinetic Resolution ◽  
Primary Amines ◽  
Dynamic Kinetic Resolution ◽  
Palladium Nanoparticle ◽  
Nanoparticle Catalyst

scholarly journals Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 2003 ◽  
Author(s):  
Takatsugu Murata ◽  
Tatsuya Kawanishi ◽  
Akihiro Sekiguchi ◽  
Ryo Ishikawa ◽  
Keisuke Ono ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
High Selectivity ◽  
Optically Active ◽  
Acyl Transfer ◽  
Chiral Compounds ◽  
Tertiary Amide

Various optically active 2-hydroxyamide derivatives are produced based on the kinetic resolution of racemic 2-hydroxyamides with a diphenylacetyl component and (R)-benzotetramisole ((R)-BTM), a chiral acyl-transfer catalyst, via asymmetric esterification and acylation. It was revealed that a tertiary amide can be used with this novel protocol to achieve high selectivity (22 examples; s-value reaching over 250). The resulting chiral compounds could be transformed into other useful structures while maintaining their chirality.

scholarly journals Biocatalytic Acetylation of Primary Amines by Lipases under Orbital Shaking and Microwave Radiation

Biocatalysis ◽  
2015 ◽  
Vol 1 (1) ◽  
Author(s):  
Yara Jaqueline Kerber Araújo ◽  
André Luiz Meleiro Porto
Keyword(s):  
Ethyl Acetate ◽  
Microwave Radiation ◽  
Kinetic Resolution ◽  
Primary Amines ◽  
Acylating Agent ◽  
Orbital Shaking

AbstractThis paper addresses the effects of the concentration of lipases, temperature and solvent on the enzymatic acetylation of primary amines. (±)-Heptan-2-amine 1, (±)-4-phenylbutan-2-amine 2, (±)-1,2,3,4-tetrahydronaphthalen-1-amine 3 and (±)-2-methylcyclohexan-1-amine 4 were acetylated using 11 lipases to obtain amides under orbital shaking and microwave radiation. Under microwave radiation the same amines were acetylated only using the CALB. (±)-Heptan-2-amine 1 was subjected to kinetic resolution, under orbital shaking for 7 h employing CALB and ethyl acetate as acylating agent, and converted into (R)-N- (heptan-2-yl)acetamide 5 (c = 42%, 88% ee

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