Chemodivergent [3+2] and [4+2] Annulations of Isoindigos with Morita–Baylis–Hillman (MBH) Carbonates
Abstract
-amino-aryl Morita-Baylis-Hillman (MBH) carbonates for the highly efficient and selective synthesis of two types of polycyclic alkaloid scaffolds. The choice of catalyst critically determines the reaction pathway: the use of a tertiary phosphine promotes a [3+2] annulation, affording the desired products in up to 90% yields over two steps. Conversely, when DABCO is used as the catalyst, a [4+2] annulation takes place, affording the corresponding products in excellent yields (up to 96%). Furthermore, moderate to excellent enantioselectivities were attained by employing chiral catalysts.
Fields of Study & Subjects
Quinazolinone synthesis and applications
Cyclopropane Reaction Mechanisms
Catalytic C–H Functionalization Methods
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 5
- Pages
- 1661–1666
- Publication date
- 26 January 2026
- Language
- EN