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

Cited 4 time in WEB OF SCIENCE Cited 4 time in Scopus
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)
Lee, Yeon-Ju; Seo, Jeyoung; Kim, Dong-Guk; Park, Hyeung-geun; Jeong, Byeong-Seon
KIOST Author(s)
Lee, Yeon Ju(이연주)
Publication Year
2013-04
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.
ISSN
0936-5214
URI
https://sciwatch.kiost.ac.kr/handle/2020.kiost/3205
DOI
10.1055/s-0032-1317801
Bibliographic Citation
SYNLETT, v.24, no.6, pp.701 - 704, 2013
Publisher
GEORG THIEME VERLAG KG
Subject
ALPHA-AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; AZLACTONES; ALKYLATION; CONFORMATION; CATALYST; DESIGN; OXAZOL-5-(4H)-ONES; ORGANOCATALYSTS
Keywords
alpha,alpha-dialkyl-alpha-amino acid; oxazol-5(4H)-one; C(4)-alkylation; BEMP; protecting group; chemoselectivity
Type
Article
Language
English
Document Type
Article
Publisher
GEORG THIEME VERLAG KG
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