An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel-Crafts/Michael/Michael/Aldol Condensation Sequence

被引：10
作者：
Philipps, Arne R. [1 ]
Fritze, Lars [1 ]
Erdmann, Nico [1 ]
Enders, Dieter [1 ]
机构：
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
来源：
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 16期
基金：
欧洲研究理事会;
关键词：
organocatalysis; domino reaction; quadruple cascade; asymmetric catalysis; alkenylation; DIPHENYLPROLINOL SILYL ETHER; TRICYCLIC CARBON FRAMEWORKS; INFRARED ABSORBING DYES; CASCADE REACTIONS; MICHAEL-ALDOL; ENANTIOSELECTIVE SYNTHESIS; FUNCTIONALIZED CYCLOHEXANES; STEREOCENTERS; CONSTRUCTION; DERIVATIVES;
D O I：
10.1055/s-0034-1380197
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An organocatalytic quadruple cascade initiated by a Friedel-Crafts-type reaction is described. The (S)-diphenylprolinol trimethylsilyl ether catalyzed reaction yields highly functionalized cyclohexenecarbaldehydes bearing a 1,1-bis[4-(dialkylamino)phenyl]ethene moiety and three contiguous stereogenic centers. The reaction tolerates various functional groups and all products are obtained with very good diastereoselectivity and with virtually complete enantiomeric excess.
引用
收藏
页码：2377 / 2384
页数：8
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