Stereoselective azide cycloaddition to chiral cyclopentanone enamines

Tetrahedron Asymmetry

Volumn 8, Issue 13, 1997, Pages 2261-2266

  Fioravanti, Stefania ^a   Pellacani, Lucio ^a   Ricci, Damiano ^a   Tardella, Paolo A ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030873707     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00239-5     Document Type: Article

References (19)

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2. Hickmott, P. W. in The Chemistry of Enamines Part 1, Rappoport, Z., Ed.; John Wiley & Sons: New York 1994, pp. 727-871,
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5. Fioravanti, S.; Luna, G.; Pellacani, L.; Tardella, P. A. Tetrahedron 1997, 53, 4779-4786.
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7. Tsuchida, T.; Koyama, M.; Mitani, M.; Takeuchi, H. H. Bull Chem. Soc. Jpn. 1980, 53, 1189-1190. Products like 8 have never been reported before in this kind of reactions.
8. 3 Both attempts gave very complex reaction mixtures mainly constituted of isomeric functionalisation products.
9. 2Et: Pellacani, L.; Persia, F.; Tardella, P. A. Tetrahedron Lett. 1980, 21, 4967-4970.
10. The product of high pressure arylsulphonyl azide cycloaddition to a cyclopentanone silyl enol ether is known to undergo ring contraction: Dauben, W. G.; Bunce, R. A. J. Org. Chem. 1982, 47, 5042-5044.
11. Examples of highly stereoselective cycloaddition reaction of 1,3-dienes to chiral enamines have been reported. See for example: Bäckvall, J. E.; Löfström, C.; Maffei, M.; Langer, V. Tetrahedron Lett. 1992, 33, 2417-2418.
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13. Bourgois, J.; Bourgois, M.; Texier, F. Bull. Soc. Chim. Fr. 1978, 485-527; Scarpati, R.; Graziano, M. L.; Nicolaus, R. A. Gazz. Chim. Ital. 1968, 98, 681-695.
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19. Prepared according to: Stetin, C.; De Jeso, B.; Pommier, J. C. J. Org. Chem. 1985, 50, 3863-3866.