Journal
TETRAHEDRON
Volume 68, Issue 46, Pages 9397-9404Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.09.014
Keywords
Organocatalysis; Asymmetric conjugate addition; Nitroacetate; beta,gamma-Unsaturated alpha-keto ester; Hydrolysis-decarboxylation
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Funding
- National Natural Science Foundation of China [20972195, 21172270]
- Guangdong Engineering Research Center of Chiral Drugs
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Organocatalytic asymmetric conjugate addition of tert-butyl nitroacetates to beta,gamma-unsaturated alpha-keto esters has been developed. The subsequent in situ hydrolysis-decarboxylation of the adducts provided 5-nitro-2-oxopentanoates. A pyrrolidine-based thiourea-tertiary amine was identified as the best catalyst. A number of gamma-aryl, gamma-alkyl, and gamma-heteroaryl beta,gamma-unsaturated alpha-keto esters and alpha-substituted tert-butyl nitroacetates were examined in the transformation. Generally 5-nitro-2-oxopentanoates were obtained in good yields (up to 97%) and enantioselectivities (up to 94% ee). The products were readily transformed to chiral proline derivatives by catalytic hydrogenation. (C) 2012 Elsevier Ltd. All rights reserved.
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