Work

Cobalt-Catalyzed Regio-, Diastereo-, and Enantioselective Reductive Coupling of Internal Alkynes with Cyclobutenes

Year: 2025

Type: article

Abstract: Herein, we report the cobalt-catalyzed asymmetric ene–yne reductive coupling of internal alkynes and unactivated cyclobutenes. The reaction produced densely functionalized chiral vinyl cyclobutanes in up to 92% yields with excellent absolute and relative stereocontrol (>99% ee, >20:1 dr, and >20:1 E / Z ), and high >20:1 regioselectivity. The scaled-up reaction and the postsynthetic derivatizations further elucidated the efficiency of the designed protocol. The preliminary mechanistic investigations suggested the involvement of zinc-mediated low-valent cobalt(I) complex generation, oxidative ene–yne cyclization, and protonation as the key mechanistic steps.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c01695

Authors: Mamata Maiti, Subha Roy, Biplab Maji

Institution: Indian Institute of Science Education and Research Kolkata

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: Science and Engineering Research Board

Award: G8532548029