A gold-triggered dearomative spirocarbocyclization/Diels-Alder reaction cascade towards diverse bridged N-heterocycles

A rapid approach for the diversity-oriented synthesis of complex bridged polycyclic N-heterocycles from readily available starting materials in two operational steps has been developed. This strategy firstly introduces molecular diversity by an Ugi four-component reaction, and then achieves these bridged N-heterocycles via an efficient gold-triggered chemo- and diastereoselective cascade non-oxidative ortho-dearomative spirocarbocyclization/Diels-Alder reaction sequence. The application of microwave irradiation for this cascade process efficiently shortens the reaction time to 10 minutes and improves the diastereoselectivity. This journal is © The Royal Society of Chemistry.

Authors
He Y.1 , Narmon T.1 , Wu D.2 , Li Z.1 , Van Meervelt L. , Van Der Eycken E.V.
Journal
Organic and Biomolecular Chemistry
Publisher
Royal Society of Chemistry
Number of issue
43
Language
English
Pages
9529-9536
Status
Published
Link
External link
DOI
10.1039/c9ob01967g
Volume
17
Year
2019
Organizations
  • 1 Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven, B-3001, Belgium
  • 2 College of Pharmaceutical Science, Zhejiang University of Technology, 18 Chaowang Road, Hangzhou, 310014, China
  • 3 Biomolecular Architecture, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven, B-3001, Belgium
  • 4 Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya street, Moscow, 117198, Russian Federation
Keywords
Microwave irradiation; Stereoselectivity; Cascade process; Diastereo-selectivity; Diastereoselective; Diversity-oriented synthesis; Molecular diversity; N-heterocycles; Reaction cascades; Reaction sequences; Gold
Date of creation
24.12.2019
Date of change
24.12.2019
Short link
https://repository.rudn.ru/en/records/article/record/55396/
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