New chiral acetate imide enolate for stereoselective aldol reactions
作者： Claudio Palomo , Mikel Oiarbide , Alberto González , Jesús M. García , Fabienne Berrée
DOI: 10.1016/0040-4039(96)01520-1
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摘要: The chiral imide acetate 4 reacts upon lithium and titanium enolate formation conditions with aldehydes in a stereoselective manner. Remarkably, aldols obtained from aromatic α,β-unsaturated exhibited opposite stereochemistry than those aliphatic aldehydes.
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A Mordini, V Snieckus), Advances in Carbanion Chemistry ,(1996)
Jacqueline Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis ,(1995)
Derek Barton, W.David Ollis, Comprehensive organic chemistry : the synthesis and reactions of organic compounds Tetrahedron Letters. ,vol. 19, ,(1978) , 10.1016/S0040-4039(01)85753-1
Lanny S. Liebeskind, Mark E. Welker, Richard W. Fengl, Transformations of chiral iron complexes used in organic synthesis. Reactions of .eta.5-CpFe(PPh3)(CO)COCH3 and related species leading to a mild, stereospecific synthesis of .beta.-lactams Journal of the American Chemical Society. ,vol. 108, pp. 6328- 6343 ,(1986) , 10.1021/JA00280A034
David A. Evans, Thomas C. Britton, Jon A. Ellman, Contrasteric carboximide hydrolysis with lithium hydroperoxide Tetrahedron Letters. ,vol. 28, pp. 6141- 6144 ,(1987) , 10.1016/S0040-4039(00)61830-0
Wolfgang Oppolzer, Jos� Marco-Contelles, Asymmetric and ‘anti’‐Selective Aldolisations of Acetates and Propionates. Preliminary Communication Helvetica Chimica Acta. ,vol. 69, pp. 1699- 1703 ,(1986) , 10.1002/HLCA.19860690725
Yoshimitsu Nagao, Yuichi Hagiwara, Toshio Kumagai, Masahito Ochiai, Takehisa Inoue, Keiji Hashimoto, Eiichi Fujita, New C-4-chiral 1,3-thiazolidine-2-thiones: excellent chiral auxiliaries for highly diastereo-controlled aldol-type reactions of acetic acid and .alpha.,.beta.-unsaturated aldehydes Journal of Organic Chemistry. ,vol. 51, pp. 2391- 2393 ,(1986) , 10.1021/JO00362A047
David J. Ager, Indra Prakash, David R. Schaad, 1,2-Amino Alcohols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis Chemical Reviews. ,vol. 96, pp. 835- 876 ,(1996) , 10.1021/CR9500038
Lendon N. Pridgen, Ahmed F. Abdel-Magid, I. Lantos, Susan Shilcrat, Drake S. Eggleston, Chelation control in metal-assisted aldol addition reactions of .alpha.-N-halogenated imide enolates leading to predominantly anti stereoselectivity. An example of a stereocontrolled Darzens reaction Journal of Organic Chemistry. ,vol. 58, pp. 5107- 5117 ,(1993) , 10.1021/JO00071A020
David A. Evans, Dale L. Rieger, Mark T. Bilodeau, Felix Urpi, Stereoselective aldol reactions of chlorotitanium enolates. An efficient method for the assemblage of polypropionate-related synthons Journal of the American Chemical Society. ,vol. 113, pp. 1047- 1049 ,(1991) , 10.1021/JA00003A051