RING-OPENING OF CYCLOPROPANEMONOCARBOCYLATES AND 1,1-CYCLOPROPANEDICARBOXYLATES USING SAMARIUM(II) DIIODIDE (SMI2)HMPA-THF SYSTEM

Authors
YAMASHITA M OKUYAMA K OHHARA T KAWASAKI I SAKAI K NAKATA S KAWABE T KUSUMOTO M OHTA S
Citation
M. Yamashita et al., RING-OPENING OF CYCLOPROPANEMONOCARBOCYLATES AND 1,1-CYCLOPROPANEDICARBOXYLATES USING SAMARIUM(II) DIIODIDE (SMI2)HMPA-THF SYSTEM, Chemical and Pharmaceutical Bulletin, 43(12), 1995, pp. 2075-2081
Citations number
40
Categorie Soggetti
Pharmacology & Pharmacy",Chemistry
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
43
Issue
12
Year of publication
1995
Pages
2075 - 2081
Database
ISI
SICI code
0009-2363(1995)43:12<2075:ROCA1>2.0.ZU;2-A
Abstract
The cyclopropane ring in 2-substituted 1,1-cyclopropanedicarboxylates was regioselectively opened by using samarium(II) diiodide (SmI2) in a hexamethylphosphoric triamide (HMPA)-tetrahydrofuran (THF) (1:10) sys tem under mild and neutral conditions to give (2-substituted ethyl)mal onates in moderate to good yields. The cyclopropane ring in 2-substitu ted cyclopropanecarboxylates or 2-substituted 3-(trimethylsilyl)cyclop ropanecarboxylates was similarly cleaved regioselectively by using SmI 2 in a HMPA-THF (1:1) system to give 4-arylbutyrates or 4-aryl-3-(trim ethylsilyl)butyrates in 16-89% yields. The reaction mechanism of these ring-opening reactions is discussed.