Highly Stereoselective Synthesis of Fluoroalkene Dipeptides via the Novel Chromium(II)-Mediated Carbon-Fluorine Bond Cleavage/New Carbon-Carbon Bond Formation

作者：Nihei Takashi; Nishi Yuji; Ikeda Natsumi; Yokotani Saya; Ishihara Takashi; Arimitsu Satoru; Konno Tsutomu^*

来源：Synthesis (Germany), 2016, 48(6): 865-881.

DOI：10.1055/s-0035-1560390

• -fluoroallylic alcohol derivatives
• carbon-fluorine bond activation
• chromium(II) chloride
• stereoselective
• fluoroalkene bioisosteres

An efficient chromium(II)-mediated reductive coupling reaction of various CBrF2-containing molecules and aldehydes has been developed. This reaction proceeds presumably via the monofluorinated dichromium(III) intermediate generated by the carbon-fluorine bond activation, and provides a general and straightforward access to synthesize a variety of (E)- or (Z)--fluoroallylic alcohols in a highly stereoselective manner. Based on the novel reductive coupling, four types of fluoroalkene dipeptide analogues could be stereoselectively prepared.

• 出版日期2016-3