Diastereoselective Synthesis of 1,3-Diyne-Tethered Trifluoromethylcyclopropanes through a Sulfur Ylide Mediated Cyclopropanation/DBU-Mediated Epimerization Sequence

A one-pot synthesis of 1,3-diyne-tethered trifluoromethylcyclopropanes starting from 2-CF3-3,5-diyne-1-enes and sulfur ylides via a sulfur ylide mediated cyclopropanation and a DBU-mediated epimerization sequence is described in this work. This process is highly diastereoselective with broad substrate scope. Moreover, a series of synthetic transformations based on the diyne moieties were conducted smoothly, affording cyclopropanes featuring trifluoromethyl-substituted all-carbon quaternary centers.

Medienart:

E-Artikel

Erscheinungsjahr:

2020

Erschienen:

2020

Enthalten in:

Zur Gesamtaufnahme - volume:85

Enthalten in:

The Journal of organic chemistry - 85(2020), 10 vom: 15. Mai, Seite 6252-6260

Sprache:

Englisch

Beteiligte Personen:

Chen, Guo-Shu [VerfasserIn]
Yan, Xiao-Xue [VerfasserIn]
Chen, Shu-Jie [VerfasserIn]
Mao, Xiang-Yu [VerfasserIn]
Li, Zhao-Dong [VerfasserIn]
Liu, Yun-Lin [VerfasserIn]

Links:

Volltext

Themen:

Journal Article
Research Support, Non-U.S. Gov't

Anmerkungen:

Date Completed 25.01.2021

Date Revised 25.01.2021

published: Print-Electronic

Citation Status PubMed-not-MEDLINE

doi:

10.1021/acs.joc.0c00162

funding:

Förderinstitution / Projekttitel:

PPN (Katalog-ID):

NLM30883450X