Dearomatization of electron poor six-membered N-heterocycles through [3+2] annulation with aminocyclopropanes

被引：84
|
作者：
Preindl, Johannes [1 ]
Chakrabarty, Shyamal [1 ]
Waser, Jerome [1 ]
机构：
[1] Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, Inst Sci & Ingn Chim, CH-1015 Lausanne, Switzerland
来源：
CHEMICAL SCIENCE | 2017年 / 8卷 / 10期
关键词：
DONOR-ACCEPTOR CYCLOPROPANES; CATALYTIC ENANTIOSELECTIVE ADDITION; DIASTEREOSELECTIVE SYNTHESIS; CYCLOADDITION REACTIONS; DIPOLAR CYCLOADDITION; NUCLEOPHILIC DEAROMATIZATION; ASYMMETRIC DEAROMATIZATION; 1,4-DIPOLAR CYCLOADDITION; ACTIVATED CYCLOPROPANES; 3-COMPONENT REACTION;
D O I：
10.1039/c7sc03197a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Many abundant and highly bioactive natural alkaloids contain an indolizidine skeleton. A simple, high yielding method to synthesize this scaffold from N-heterocycles was developed. A wide range of pyridines, quinolines and isoquinolines reacted with donor-acceptor (DA)-aminocyclopropanes via an ytterbium(III) catalyzed [3 + 2] annulation reaction to give tetrahydroindolizine derivatives. The products were obtained with high diastereoselectivities (dr > 20 : 1) as anti-isomers. Additionally, the formed aminals could be easily converted into secondary and tertiary amines through iminium formation followed by reduction or nucleophile addition. This transformation constitutes the first example of dearomatization of electron-poor six-membered heterocycles via [3 + 2] annulation with DA cyclopropanes.
引用
收藏
页码：7112 / 7118
页数：7
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