α-Heterosubstituted Aldehydes in Organic Synthesis. Enantioselective Approaches to New Analogues of Mevinic Acids

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Title:α-Heterosubstituted Aldehydes in Organic Synthesis. Enantioselective Approaches to New Analogues of Mevinic Acids
Creators:
Enders, Dieter
Burkamp, Frank
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 68, 5, pp. 975-1006
Uncontrolled Keywords:Mukaiyama reaction, Aldol reactions, HMG-CoA-reductase inhibitors, SAMP, TADDOL, Amino aldehydes, Stereoselective reactions, Asymmetric synthesis, Lactones

Abstract

Various aldol approaches towards the asymmetric synthesis of the lactone moiety of HMG-CoA-reductase inhibitors are described. Auxiliary controlled as well as catalytic aldol reactions resulted only in modest to low selectivities, whereas 1,2-additions to readily available highly enantiomerically enriched α-heterosubstituted aldehydes yielded δ-hydroxy-β-ketoesters with a high degree of diastereocontrol and in good chemical yields. The novel mevinic acid analogues could then be obtained by <i>syn</i>-reduction of the addition products. <p>

Title:α-Heterosubstituted Aldehydes in Organic Synthesis. Enantioselective Approaches to New Analogues of Mevinic Acids
Creators:
Enders, Dieter
Burkamp, Frank
Uncontrolled Keywords:Mukaiyama reaction, Aldol reactions, HMG-CoA-reductase inhibitors, SAMP, TADDOL, Amino aldehydes, Stereoselective reactions, Asymmetric synthesis, Lactones
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:68
Number:5
Page Range:pp. 975-1006
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20030975UNSPECIFIED
ID Code:2098
Item Type:Article
Deposited On:06 Feb 2009 17:15
Last Modified:06 Feb 2009 16:15

Citation

Enders, Dieter; Burkamp, Frank (2003) α-Heterosubstituted Aldehydes in Organic Synthesis. Enantioselective Approaches to New Analogues of Mevinic Acids. Collection of Czechoslovak Chemical Communications, 68 (5). pp. 975-1006. ISSN 0010-0765

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