Work

Asymmetric Synthesis of Tetrahydrofurans through Palladium(0)-Catalyzed [3 + 2]-Cycloaddition of Vinylcyclopropanes with Ketenes

Year: 2019

Type: article

Abstract: In this article we describe a new asymmetric synthesis of highly substituted tetrahydrofurans through a Pd(PPh 3 ) 4 -catalyzed formal [3 + 2]-cycloaddition of donor–acceptor cyclopropanes and ketenes. The desired structural motif was formed in moderate to excellent yields (42–84% for 16 examples), with excellent Z: E isomer diastereoselectivity (≥19:1 for 16 examples), and with good to excellent enantioselectivity in all cases examined (83–97% ee for 6 examples). The synthetic utility of the products was illustrated by a number of diastereoselective transformations into reduced tetrahydrofurans and spirocyclic tetrahydrofuran-barbiturate derivatives.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.9b01854

Authors: Mukulesh Mondal, Manashi Panda, Vickie McKee, Nessan J. Kerrigan

Institutions: Oakland University, University of Southern Denmark, Dublin City University

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Carlsbergfondet, Division of Chemistry

Awards: G4270259643, G5867436061