Pregled bibliografske jedinice broj: 1794
A Highly Stereocontrolled Synthesis of S-(-)-1-(4-tert-Butyl)phenyl-2-methyl-3-N-(cis-3, 5-dimethyl)morpholinylpropane via Chiral Mannich Reaction
A Highly Stereocontrolled Synthesis of S-(-)-1-(4-tert-Butyl)phenyl-2-methyl-3-N-(cis-3, 5-dimethyl)morpholinylpropane via Chiral Mannich Reaction // Tetrahedron, 53 (1997), 2; 689-696 doi:10.1016/S0040-4020(96)01011-3 (međunarodna recenzija, članak, znanstveni)
CROSBI ID: 1794 Za ispravke kontaktirajte CROSBI podršku putem web obrasca
Naslov
A Highly Stereocontrolled Synthesis of S-(-)-1-(4-tert-Butyl)phenyl-2-methyl-3-N-(cis-3, 5-dimethyl)morpholinylpropane via Chiral Mannich Reaction
Autori
Vinković, Vladimir ; Šunjić, Vitomir
Izvornik
Tetrahedron (0040-4020) 53
(1997), 2;
689-696
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
Chemoenzymatic synthesis. Substituted morpholines. Stereochemical aspects. Carbonyl-compounds. Enamine synthesis
Sažetak
By employing cis-2, 6-dimethylmorpholinemethylene immonium tetrachloroaluminate (5) enamines 9 and 10, prepared from 4-tert-butylpropiophenone and propiophenone with (R)-(-)-2-(methoxymethyl)pyrrolidine (8), were converted to chiral Mannich bases 11, 12 with nearly 100% ee ; optical purity of these β -amino ketones drops significantly during isolation. Two-step reduction of the keto group in 11, 12 afforded (S)-(-)-3-(4-tert-Butyl)phenyl-1-N-(cis-2, 6-dimethyl)morpholinyl-2-methylpropane (1), (S)-enantiomer of racemic systemic fungicide, generic name fenpropimorph, and its congener 13 with 95.1% and 90.7% ee, respectively. A mechanistic model for asymmetric induction in the diastereoselective step is proposed.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
Citiraj ovu publikaciju:
Časopis indeksira:
- Current Contents Connect (CCC)
- Web of Science Core Collection (WoSCC)
- Science Citation Index Expanded (SCI-EXP)
- SCI-EXP, SSCI i/ili A&HCI
- Scopus
