Catalytic Asymmetric Synthesis of [2,3]-Fused Indoline Heterocycles through Inverse-Electron-Demand Aza-Diels-Alder Reaction of Indoles with Azoalkenes

An unprecedented catalytic asymmetric inverse‐electron‐demand aza‐Diels–Alder reaction of indoles with in situ formed azoalkenes is reported. A diverse set of [2,3]‐fused indoline heterocycles were achieved in generally good yields (up to 97 %) with high regioselectivity and diastereoselectivity (&g...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2014-04, Vol.53 (18), p.4680-4684
Main Authors: Tong, Min-Chao, Chen, Xuan, Li, Jun, Huang, Rong, Tao, Haiyan, Wang, Chun-Jiang
Format: Article
Language:English
Subjects:
Alkenes - chemistry
asymmetric catalysis
Asymmetry
Aza Compounds - chemistry
azoalkenes
Catalysis
Catalysts
cycloaddition
Cycloaddition Reaction
Demand
Electrons
Heterocyclic Compounds - chemical synthesis
Indoles
Indoles - chemistry
indolines
Molecular Structure
Stereoisomerism
Synthesis
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Summary:An unprecedented catalytic asymmetric inverse‐electron‐demand aza‐Diels–Alder reaction of indoles with in situ formed azoalkenes is reported. A diverse set of [2,3]‐fused indoline heterocycles were achieved in generally good yields (up to 97 %) with high regioselectivity and diastereoselectivity (>20:1 d.r.), and with excellent enantioselectivity (up to 99 % ee). In(verse) demand: The unprecedented catalytic asymmetric inverse‐electron‐demand aza‐Diels–Alder reaction of indoles with in situ formed azoalkenes is reported. A diverse set of [2,3]‐fused indoline heterocycles were produced in generally good yields with high regioselectivity and diastereoselectivity, and with excellent enantioselectivity.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201400109