Palladium-catalyzed Hydrophosphorylation and Hydrophosphinylation of Cyclopropenes

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2008 Jul 1

PMID 18588304

Citations 8

Authors

Bassam K Alnasleh

William M Sherrill

Michael Rubin

Affiliations

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Abstract

Novel transition-metal-catalyzed addition of P-H entities across the cyclopropene double bond has been developed. This transformation allows for mild and efficient preparation of phosphorus-containing cyclopropanes in good yields and high degrees of diastereoselectivity.

Citing Articles

Copper-Phosphido Catalysis: Enantioselective Addition of Phosphines to Cyclopropenes.

Daniels B, Hou X, Corio S, Weissman L, Dong V, Hirschi J Angew Chem Int Ed Engl. 2023; 62(36):e202306511.

PMID: 37332088 PMC: 11365472. DOI: 10.1002/anie.202306511.

Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann's purple.

Filatov A, Khoroshilova O, Larina A, Boitsov V, Stepakov A Beilstein J Org Chem. 2022; 18:769-780.

PMID: 35859623 PMC: 9263550. DOI: 10.3762/bjoc.18.77.

Copper-Catalyzed Enantio- and Diastereoselective Addition of Silicon Nucleophiles to 3,3-Disubstituted Cyclopropenes.

Zhang L, Oestreich M Chemistry. 2019; 25(63):14304-14307.

PMID: 31531992 PMC: 6899982. DOI: 10.1002/chem.201904272.

Intramolecular nucleophilic addition of carbanions generated from N-benzylamides to cyclopropenes.

Maslivetc V, Barrett C, Aksenov N, Rubina M, Rubin M Org Biomol Chem. 2017; 16(2):285-294.

PMID: 29242861 PMC: 5755969. DOI: 10.1039/c7ob02068f.

Directed nucleophilic addition of phenoxides to cyclopropenes.

Yamanushkin P, Lu-Diaz M, Edwards A, Aksenov N, Rubina M, Rubin M Org Biomol Chem. 2017; 15(38):8153-8165.

PMID: 28920624 PMC: 5629095. DOI: 10.1039/c7ob01785e.