Highly stereoselective aldol reactions of lithium ester enolates with (Rs)-2-(p-tolylsulfinyl)cyclohexanones

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9462-9470

  García Ruano, José L ^a   Barros, David ^a   Maestro, M Carmen ^a   Araya Maturana, Ramiro ^b   Fischer, Jean ^c  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSITY OF CHILE   (Chile)

^c UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000918006     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961643t     Document Type: Article

References (42)

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27. When the reaction was carried out on direct addition mode (ester enolate was added over the keto sulfoxide), the yield diminished drastically.
28. Starting from 2a + 2b or 3a + 3b diastereoisomeric mixtures, only the the major component can be isolated by chromatography.
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30. This mixture, enriched in the minor diastereoisomer 2b, was prepared from the original mixture by repeated crystallizations of the major one 2a.
31. 3 as chiral shift reagent.
32. The axial approach on the cyclohexanone ring must be favored when the attack of the reagent takes place on the presumably minor conformations of these cyclohexanones (those arranging the sulfinyl group in axial position), because the steric interactions with the substituent must be more severe than those with the syn-diaxial protons. Nevertheless, the diastereoisomer formed from this attack would be the same as that obtained by the equatorial approach on the major conformation of the substrates.
33. Maestro, M. A.; Castedo, L.; Mouriño, A. J. Org. Chem. 1992, 57, 5208.
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35. Back, T. G.; Baron, D. L.; Yang K. J. Org. Chem. 1993, 58, 2407.
36. 2 or Raney nickel.
37. We refer to the stereoisomeric enolates as Z or E, assigning to the "OLi" a higher priority than "OR" group.
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40. 1H NMR parameters. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
41. In the reported conditions for lactone simultaneous cleavage and O-alkylation (King, S. A. J. Org. Chem. 1994,59, 2253), compound 18 afforded exclusively cleavage.
42. Diem, M. J.; Burow, D. F.; Fry, J. L. J. Org. Chem. 1977, 42, 1801.