Asymmetric Organocatalytic Cascade Reactions with α-Substituted α,β-Unsaturated Aldehydes

被引:131
作者
Galzerano, Patrizia [1 ]
Pesciaioli, Fabio [1 ]
Mazzanti, Andrea [1 ]
Bartoli, Giuseppe [1 ]
Melchiorre, Paolo [1 ,2 ]
机构
[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
[2] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
关键词
aldehydes; cascade reactions; molecular complexity; organocatalysis; quaternary stereocenters; CHIRAL PRIMARY AMINE; IMINIUM ACTIVATION; DOMINO REACTIONS; CATALYSIS; KETONES; ENONES; AMINOCATALYSIS; STEREOCENTERS; ALKYLATION; CHEMISTRY;
D O I
10.1002/anie.200903803
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Time to α-branch out! The first highly enantioselective aminocatalytic activation of a-substituted αβ-unsaturated aldehydes is presented. The chiral primary amine 1 selectively activates ct-branched enals toward a well-defined iminium ion enamine reaction sequence for both Friedel-Crafts/amination and sulfa-Michael/ amination cascades. The valuable multifunctional products, having two contiguous sterocenters, are isolated in high enantiomeric purity. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7892 / 7894
页数:3
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