Ring opening of cyclopropanemonocarboxylates and 1,1- cyclopropanedicarboxylates using samarium(II) diiodide (SmI2)-HMPA-THF system

DOI: 10.1248/cpb.43.2075

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 2075 - 2081 (1995)

Update date:2022-08-04

Topics:

Authors:

Yamashita

Okuyama Okuyama

Ohhara Ohhara

Kawasaki

Sakai Sakai

Nakata Nakata

Kawabe Kawabe

Kusumoto

Ohta Ohta

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Article abstract of DOI:10.1248/cpb.43.2075

The cyclopropane ring in 2-substituted 1,1-cyclopropanedicarboxylates was regioselectively opened by using samarium(II) diiodide (Sml₂) in a hexamethylphosphoric triamide (HMPA)-tetrahydrofuran (THF) (1:10) system under mild and neutral conditions to give (2-substituted ethyl)malonates in moderate to good yields. The cyclopropane ring in 2-substituted cyclopropanecarboxylates or 2-substituted 3- (trimethylsilyl)cyclopropanecarboxylates was similarly cleaved regioselectively by using Sml₂ in a HMPA-THF (1:1) system to give 4- arylbutyrates or 4-aryl-3-(trimethylsilyl)butyrates in 16-89% yields. The reaction mechanism of these ring-opening reactions is discussed.

Full text of DOI:10.1248/cpb.43.2075

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