Synthesis of Spirocyclic 1‐Pyrrolines from Nitrones and Arynes through a Dearomative [3,3′]‐Sigmatropic Rearrangement

• Published in: Angewandte Chemie International Edition Vol. 59; no. 35; pp. 15244 - 15248
• Main Authors: Alshreimi, Abdullah S., Zhang, Guanqun, Reidl, Tyler W., Peña, Ricardo L., Koto, Nicholas‐George, Islam, Shahidul M., Wink, Donald J., Anderson, Laura L.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 24.08.2020; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Cascade chemical reactions; Chemistry; Chemistry, Multidisciplinary; Cycloaddition; dearomatization; dipolar cycloaddition; Divergence; nitrones; Physical Sciences; Pyrrolidine; Science & Technology; sigmatropic rearrangement; spirocyclic pyrroline; Stereoselectivity; dearomatization; CATALYTIC ASYMMETRIC DEAROMATIZATION; dipolar cycloaddition; CLAISEN REARRANGEMENT; INTRAMOLECULAR DEAROMATIZATION; INDOLES; AMINO-ACIDS; 1,3-DIPOLAR CYCLOADDITION; CONSTRUCTION; nitrones; spirocyclic pyrroline; PHENOL DEAROMATIZATION; STEREOGENIC CENTERS; sigmatropic rearrangement; DERIVATIVES

A dearomative [3,3′]‐sigmatropic rearrangement that converts N‐alkenylbenzisoxazolines into spirocyclic pyrroline cyclohexadienones has been developed by using the dipolar cycloaddition of an N‐alkenylnitrone and an aryne to access these unusual transient rearrangement precursors. This cascade react...