A convenient oxazole C-2 protecting group: the synthesis of 4- and 5-substituted oxazoles via metalation of 2-triisopropylsilyloxazoles.
[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.
Miller
Ross A
RA
Department of Process Research, Merck Research Laboratories, Rahway, New Jersey 07065, USA. ross_miller@merck.com
Smith
Randi M
RM
Marcune
Benjamin
B
D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry*
D010080:Oxazoles; D008094:Lithium