Asymmetric propionate aldol reactions of a chiral lithium enolate accessible from direct enolization with n-butyllithium

Arkivoc

Volumn 2005, Issue 6, 2005, Pages 377-392

  Palomo, Claudio ^a   Oiarbide, Mikel ^a   Gómez Bengoa, Enrique ^a   Mielgo, Antonia ^a   González Rego, M Concepción ^a   García, Jesús M ^b   González, Alberto ^b   Odriozola, José M ^b   Bañuelos, Patricia ^b   Linden, Anthony ^c  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b PUBLIC UNIVERSITY OF NAVARRE   (Spain)

^c UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Aldol reaction; Asymmetric synthesis; Butyllithium; Hapalosin; Lithium enolates

Indexed keywords

EID: 24044468663     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (54)

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40. See the Supporting Information for details.
41. This result would be in agreement with the fact that the OSiiPr3 group has no ability to chelate. See: (a) Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1990, 112, 6130.
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43. Slightly lower levels of diastereoselection were observed when the lithium enolate of 5 was generated under the more standard LDA-TMEDA or LDA-HMPA conditions in THF.
44. 3, c=1.2) (Heathcock, C. H.; White, C. T.; Morrison, J. J.; Van Derveer, D. J. J. Org. Chem. 1981, 46, 1296).
45. CCDC-204883-204885 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
46. 25 = +42.2 (EtOH, c = 1.0)).
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54. Compound 16 was prepared starting from (1S)-(-)-camphor by following the same procedure employed for the preparation of 5 from the (1R)-enantiomer.