A gold-triggered dearomative spirocarbocyclization/Diels–Alder reaction cascade towards diverse bridged N-heterocycles. Issue 43 (30th October 2019)

• Record Type: Journal Article
• Authors: He, Yi; Narmon, Thomas; Wu, Danjun; Li, Zhenghua; Van Meervelt, Luc; Van der Eycken, Erik V.
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 43(2019)
• Page Start: 9529
• Page End: 9536
• Publication Date: 2019-10-30
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob01967g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An efficient chemo- and diastereoselective gold-triggered post-Ugi non-oxidative ortho -dearomative spirocarbocyclization/Diels–Alder reaction cascade sequence has been developed to deliver diverse bridged polycyclic N-heterocycles. Abstract : 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.