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
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- Title
- BEMP-Promoted C(4)-Alkylation of 4-Alkyloxazol-5(4H)-ones: A Rapid and Efficient Route to alpha,alpha-Dialkyl-alpha-amino Acids
- KIOST Author(s)
- Lee, Yeon Ju(이연주)
- Alternative Author(s)
- 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
- 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
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- There are no files associated with this item.
