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Synfacts 2014; 10(1): 0054
DOI: 10.1055/s-0033-1340455
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

N,N′-Dioxide–Scandium(III)-Catalyzed Asymmetric Michael Addition

Contributor(s):
Hisashi Yamamoto
,
Fengtao Zhou
Ji J, Lin L, Zhou L, Zhang Y, Liu Y, Liu X, Feng X * Sichuan University, Chengdu, P. R. of China
N,N′-Dioxide–Scandium(III)-Catalyzed Asymmetric Michael Addition of β,γ-Unsaturated Butenolides to α,β-Unsaturated γ-Keto Esters.

Adv. Synth. Catal. 2013;
355: 2764-2768
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Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

α,β-unsaturated γ-keto esters - γ-butenolides - N,N′-dioxides - Michael addition - scandium

Significance

Butenolide derivatives represent an important structural motif in natural products and pharmaceuticals. The authors develop a highly efficient catalytic system for the asymmetric vinylogous Michael addition of γ-substituted butenolides to α,β-unsaturated γ-keto esters, leading to γ,γ-disubstituted butenolides in good yield and excellent enantioselectivities.


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Comment

The substrate scope of this reaction is well investigated. The ester groups of the α,β-unsaturated γ-keto esters display an influence on both diastereo- and enantioselectivity. The bulkier γ-substituted groups in the butenolides lead to the increase of diastereo- and enantioselectivity, but the reactivities decrease obviously. Aromatic and aliphatic unsaturated γ-keto esters are well tolerated.


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