title: A convenient oxazole C-2 protecting group: the synthesis of 4- and 5-substituted oxazoles via metalation of 2-triisopropylsilyloxazoles.
abstract: [reaction: see text] Metalation of oxazoles at the 4 and 5 position was achieved after regioselective C-2 silyl protection. Removal of the protecting group was then accomplished under mild conditions allowing for a straightforward preparation of C-5 monosubstituted and C-4,5 disubstituted oxazoles. The first practical C-2 protecting group of oxazoles has been demonstrated.
authors.affiliation: Department of Process Research, Merck Research Laboratories, Rahway, New Jersey 07065, USA. ross_miller@merck.com
authors.forename: Ross A
authors.initials: RA
authors.lastname: Miller
authors.forename: Randi M
authors.initials: RM
authors.lastname: Smith
authors.forename: Benjamin
authors.initials: B
authors.lastname: Marcune
mesh_terms: D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D010080:Oxazoles; D008094:Lithium