BEMP-Promoted C(4)-Alkylation of 4-Alkyloxazol-5(4H)-ones: A Rapid and Efficient Route to alpha,alpha-Dialkyl-alpha-amino Acids

Title
BEMP-Promoted C(4)-Alkylation of 4-Alkyloxazol-5(4H)-ones: A Rapid and Efficient Route to alpha,alpha-Dialkyl-alpha-amino Acids
Author(s)
정병선이연주[이연주]서재영[서재영]김동국박형근[박형근]
Keywords
ALPHA-AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; AZLACTONES; ALKYLATION; CONFORMATION; CATALYST; DESIGN; OXAZOL-5-(4H)-ONES; ORGANOCATALYSTS
Issue Date
201304
Publisher
GEORG THIEME VERLAG KG
Citation
SYNLETT, v.24, no.6, pp.701 - 704
Abstract
Rapid and efficient C(4)-alkylation of 4-alkyloxazol-5(4H)-ones has been achieved by the utilization of BEMP as base. 4,4-Dialkyloxazol-5(4H)-ones, which can easily be hydrolyzed into free alpha,alpha-dialkyl-alpha-amino acids, were obtained in high yields (up to 99%) within a few minutes (1-18 min). BEMP, a sterically hindered strong base with low nucleophilicity facilitated the desired reaction, while decreasing the rate of side reactions such as O-alkylation, C(2)-alkylation and the breakage of oxazolone.
URI
http://hdl.handle.net/YU.REPOSITORY/26062http://dx.doi.org/10.1055/s-0032-1317801
ISSN
0936-5214
Appears in Collections:
약학대학 > 약학부 > Articles
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