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Titolo:
DERACEMIZATION OF COMPOUNDS POSSESSING A SEC-ALCOHOL OR SEC-AMINO GROUP THROUGH A CYCLIC OXIDATION-REDUCTION SEQUENCE - A KINETIC TREATMENT
Autore:
KROUTIL W; FABER K;
Indirizzi:
GRAZ TECH UNIV,INST ORGAN CHEM,STREMAYRGASSE 16 A-8010 GRAZ AUSTRIA GRAZ TECH UNIV,INST ORGAN CHEM A-8010 GRAZ AUSTRIA
Titolo Testata:
Tetrahedron : asymmetry
fascicolo: 16, volume: 9, anno: 1998,
pagine: 2901 - 2913
SICI:
0957-4166(1998)9:16<2901:DOCPAS>2.0.ZU;2-G
Fonte:
ISI
Lingua:
ENG
Soggetto:
ENANTIOSPECIFIC OXIDATION; DYNAMIC RESOLUTIONS; MICROBIAL OXIDATION; ENZYMATIC OXIDATION; ACID PRODUCTION; OXIDASE; STEREOINVERSION; COMBINATION; ENANTIOMERS; CONVERSION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Science Citation Index Expanded
Science Citation Index Expanded
Citazioni:
38
Recensione:
Indirizzi per estratti:
Citazione:
W. Kroutil e K. Faber, "DERACEMIZATION OF COMPOUNDS POSSESSING A SEC-ALCOHOL OR SEC-AMINO GROUP THROUGH A CYCLIC OXIDATION-REDUCTION SEQUENCE - A KINETIC TREATMENT", Tetrahedron : asymmetry, 9(16), 1998, pp. 2901-2913

Abstract

Deracemization of compounds bearing a chiral sec-hydroxy or -amino group can be achieved in a one- pot reaction via a novel process consisting of a cyclic oxidation-reduction sequence. Thus, in the first step,one enantiomer from the racemic starting material (R+S) is enantioselectively oxidized forming an achiral intermediate product (P, a ketoneor imine, respectively). In the second step, the latter is non-selectively reduced to give al:ain R+S in racemic form. Cyclic repetition ofthis oxidation-reduction sequence leads to an overall chiral inversion of the faster reacting enantiomer from the racemic starting materialto yield the slower reacting enantiomer as the final product in a theoretical 100% chemical and enantiomeric yield. Mathematical treatment of the kinetics of this 'cyclo-process' allowed the estimation of the practical feasibility at hand of two crucial parameters: (i) the maximal obtainable enantiomeric excess and (ii) the number of cycles required (expressed as theoretical turnover) to reach equilibrium. A computer program for analysis and optimization of such processes was developed, which is available via the Internet. (C) 1998 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 05/12/20 alle ore 19:13:50