Highly Enantioselective Synthesis of α-Amino Acid Derivatives by an NHC-Catalyzed Intermolecular Stetter Reaction

被引:189
作者
Jousseaume, Thierry [1 ]
Wurz, Nathalie E. [1 ]
Glorius, Frank [1 ]
机构
[1] Univ Munster, Inst Organ Chem, Corrensstr 40, D-48149 Munster, Germany
关键词
amino acids; asymmetric catalysis; N-heterocyclic carbene; organocatalysis; protonation; N-HETEROCYCLIC CARBENE; CONJUGATE ADDITION-PROTONATION; HYDROGEN-ATOM TRANSFER; ACTIVATED DOUBLE-BONDS; 1,4-ADDITION/ENANTIOSELECTIVE PROTONATION; NONADJACENT STEREOCENTERS; ENOLATE PROTONATIONS; ASYMMETRIC-SYNTHESIS; CASCADE REACTION; ALDEHYDES;
D O I
10.1002/anie.201006548
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
PROTONtype: An NHC-catalyzed (NHC=N-heterocyclic carbene), highly asymmetric intermolecular Stetter reaction allows the atom-economic and efficient formation of valuable α-amino acid derivatives (see scheme); the key step is an intramolecular stereoselective protonation. For the first time, a β-unsubstituted Michael acceptor was employed successfully in this kind of reaction, most importantly, with a broad range of different aldehydes. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:1410 / 1414
页数:5
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