Nitrogen-interrupted halo-Prins/halo-Nazarov fragment coupling cascade for the synthesis of indolines.

ABSTRACT: The nitrogen-interrupted Nazarov cyclization can be a powerful method for the stereocontrolled synthesis of sp³-rich N-heterocycles. However, due to the incompatibility between the basicity of nitrogen and the acidic reaction conditions, examples of this type of Nazarov cyclization are scarce. Herein, we report a one-pot nitrogen-interrupted halo-Prins/halo-Nazarov coupling cascade that joins two simple building blocks, an enyne and a carbonyl partner, to furnish functionalized cyclopenta[b]indolines with up to four contiguous stereocenters. For the first time, we provide a general method for the alkynyl halo-Prins reaction of ketones, thus enabling the formation of quaternary stereocenters. Additionally, we describe the outcomes of secondary a

SUBMITTER: Milosavljevic A 

PROVIDER: S-EPMC10208031 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature