In search of high stereocontrol for the construction of cis-disubstituted cyclopropane compounds. Total synthesis of a cyclopropane-configured urea-PETT analogue that is a HIV-1 reverse transcriptase inhibitor.
[reaction: see text] A new azetidine-ligated dirhodium(II) catalyst that possesses a l-menthyl ester attachment provides significant diastereocontrol and high enantiocontrol for the formation of cis-cyclopropane products from reactions of substituted styrenes with diazo esters.
Hu
Wenhao
W
Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA.
Timmons
Daren J
DJ
Doyle
Michael P
MP
D003521:Cyclopropanes / Q000138:chemical synthesis*; D054303:HIV Reverse Transcriptase / Q000037:antagonists & inhibitors*; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003521:Cyclopropanes; D018894:Reverse Transcriptase Inhibitors; D054303:HIV Reverse Transcriptase