Pregled bibliografske jedinice broj: 16091
Stereoselective cyclopropanation and ring-opening: application to the synthesis of pure (S)-2-methyl-3-arylpropylamines
Stereoselective cyclopropanation and ring-opening: application to the synthesis of pure (S)-2-methyl-3-arylpropylamines // Tetrahedron, 54 (1998), 31; 9123-9128 doi:10.1016/S0040-4020(98)00549-3 (međunarodna recenzija, članak, znanstveni)
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Naslov
Stereoselective cyclopropanation and ring-opening: application to the synthesis of pure (S)-2-methyl-3-arylpropylamines
Autori
Roje, Marin ; Vinković, Vladimir ; Šunjić, Vitomir ; Solladie-Cavallo, Arlette ; Diep-Vohuule, Ahn ; Isarno, Thomas
Izvornik
Tetrahedron (0040-4020) 54
(1998), 31;
9123-9128
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
Optically-active siloxycyclopropanes ; Chemoenzymatic synthesis ; Asymmetric catalysis ; Substituted cyclopropanes ; Hydrogenolysis ; Regioselectivity ; Ligands
Sažetak
Stereoselective catalytic and stoichiometric cyclopropanation of styrenes 3a, 3b was studied ; stoichiometric method turned out superior in the terms of enantioselectivity. The intermediary carboxymethyl cyclopropane 11a, 11b, obtained on reduction of carbethoxy derivatives 4a, 4b, were hydrogenolyzed to (S)-1, 3-substituted-2-methylpropanes 15a, 15b. The highest conversion and regioselectivity was obtained with 3% Pd/C as the catalyst. The final steps, chlorination of alcohol 15a into 19a, and alkylation of cyclic sec amines were already demonstrated by us (ref. 2c) to afford (S)-(-)-2-(4-tert-butylphenyl)-1-cis-2, 6-dimethylmorpholyl)propane (S-1a) and (S)-(-)-2-(4-tert-butylphenyl)-1-piperidylpropane (S-2a), the (S)-enantiomers of two systemic fungicides presently commercialized as racemates, without any lost of enantiomeric purity.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
