Stereoselective synthesis of novel chimerical amino acids via a photochemical key step

Synlett

Volumn , Issue 9, 1999, Pages 1465-1467

  Wessig, Pablo ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

Amino acid; Cyclizations; Photochemistry; Radical reactions; Stereoselective synthesis

Indexed keywords

AMINO ACID DERIVATIVE; BENZOPHENONE; PROLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIMERA; CHIRALITY; CYCLIZATION; NONHUMAN; PHOTOCHEMISTRY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032845097     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2843     Document Type: Article

References (20)

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13. 6 calcd. C 69.96, H 6.31, N 3.02; found C 70.00, H 6.41, N 2.92.
14. 2 g (4.32 mmol) 6e was dissolved in a mixture of 50 ml MeOH and 4.3 ml cyclohexene and 0.5 g Pd/C (10% Pd). The mixture was refluxed for 1.5 h, filtered through a pad celite and evaporated giving 1.08 g (76%) 7. The crystallographic data of 7 were deposited as "supplementary publication no. CCDC-120118" at the Cambridge Crystallographic Data Centre. Copies of the data may be received free of charge at the following address: CCDC, 12 Union Road, Cambridge CB21EZ (Fax: (+44) 1223-336-033; E-mail: deposit@ccdc.cam.ac.uk).
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19. The Cbz group was replaced by a methoxycarbonyl group to simplify the calculations. Low energy conformers were selected by preliminary investigations on semiempirical level (PM3). These geometries were optimized at UHF/3-21G level and characterized by frequency analysis. Improved energies were obtained at UB3PW91/6-31G* level. All calculations were performed with the ab initio package Gaussian 98. Energies and geometry data of these calculations are available upon request. In Scheme 4 all hydrogen atoms are omitted except that of the OH-group.
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