Regioselective functionalization of the oxazole scaffold using TMP-bases of Mg and Zn.
A general method for the synthesis of 2,4,5-trisubstituted oxazoles has been developed. Starting from commercially available oxazole, successive metalations using TMPMgCl·LiCl or TMPZnCl·LiCl led to the corresponding magnesiated or zincated species which were stable toward ring fragmentation. Furthermore, they readily reacted with various electrophiles, such as aryl and allylic halides, acid chlorides, TMSCl, and TMS-CN, providing highly functionalized oxazoles.
Department of Chemistry, Ludwig-Maximilians-University , Butenandtstrasse 5-13, 81377 München, Germany, and Bayer CropScience AG, Industriepark Höchst, 65926 Frankfurt am Main, Germany.
Diana
D
Haas
Marc
M
Mosrin
Paul
P
Knochel
D008094:Lithium / Q000737:chemistry; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010880:Piperidines / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D009942:Organometallic Compounds; D010080:Oxazoles; D010880:Piperidines; C551336:2,2,6,6-tetramethylpiperidide; D008094:Lithium; D008274:Magnesium; D015032:Zinc