- Nanomole-scale assignment of configuration for primary amines using a kinetic resolution strategy
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The absolute configurations of primary amines were assigned using a kinetic resolution strategy with Mioskowski's enantioselective 1-(R,R) and 2-(S,S) acylating agents. A simple mnemonic was developed to determine the configuration. A pseudoenantiomeric pair of reagents, 1-(R,R) and 2-(S,S)-d 3, was prepared and used to assay primary amines on a micromolar scale. The ESI-MS readout of the resulting acetamide products reproduced the selectivity factors from kinetic experiments. The method can be used on mixtures of amines and was validated with amine samples as small as 50 nmol.
- Miller, Shawn M.,Samame, Renzo A.,Rychnovsky, Scott D.
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supporting information
p. 20318 - 20321
(2013/02/23)
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- Lipase-catalysed Enantioselective Acylation of N-Protected or Unprotected 2-Aminoalkan-1-ols
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Porcine pancreatic lipase (PPL) catalysed the acylation of 2-aminoalkan-1-ols; the enantiospecificity depends on the starting amino alcohol.The catalytic activity of the enzyme was markedly improved when the benzyl carbamate derivatives were used as substrates; in general, the enzyme displayed a high enantiospecificity.
- Fernandez, Susana,Brieva, Rosario,Rebolledo, Francisca,Gotor, Vicente
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p. 2885 - 2890
(2007/10/02)
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- LIPASE-CATALYSED KINETIC RESOLUTION OF N,O-DIACETYL-2-AMINO-1-BUTANOL IN DIISOPROPYL ETHER
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N,O-Diacetyl-2-amino-1-butanol (2) on lipase-catalysed transesterification with 1-butanol in diisopropyl ether gave (S)-(-)-2 and (R)-(+)-N-acetyl-2-amino-1-butanol (3); proper stereochemistry and correct optical rotations of chiral 2 and 3, incorrectly reported in literature, were determined after their conversion to chiral 2-amino-1-butanol (1).
- Bevinakatti, Hanamanthsa S.,Newadkar, Ravindra V.
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p. 583 - 586
(2007/10/02)
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- Enantioselective Acylation of Amino Alcohols by Porcine Pancreatic Lipase
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Porcine pancreatic lipase catalysed the enantioselective acylation of the amino group of 1-aminopropan-2-ol and the N- and O-acylation of 2-aminobutan-1-ol.
- Gotor, Vicente,Brieva, Rosario,Rebolledo, Francisca
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p. 957 - 958
(2007/10/02)
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