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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Kawabata, Takeo Yang, Pan Uyama, Makoto Hayashi, Kazuhiro Hyakutake, Ryuichi Yoshimura, Tomoyuki Tomohara, Keisuke Takuwa, Masatoshi Tokitoh, Norihiro Sasamori, Takahiro |
| Description | Author Affiliation: Yoshimura T ( Institute for Chemical Research, Kyoto University, Uji 611-0011, Japan.) |
| Abstract | β-Lactams with contiguous tetra- and trisubstituted carbon centers were prepared in a highly enantioselective manner through 4-exo-trig cyclization of axially chiral enolates generated from readily available α-amino acids. Use of a weak base (metal carbonate) in a protic solvent (EtOH) is the key to the smooth production of β-lactams. Use of the weak base is expected to generate the axially chiral enolates in a very low concentration, which undergo intramolecular conjugate addition without suffering intermolecular side reactions. Highly strained β-lactam enolates thus formed through reversible intramolecular conjugate addition (4-exo-trig cyclization) of axially chiral enolates undergo prompt protonation by EtOH in the reaction media (not during the work-up procedure) to give β-lactams in up to 97 % ee. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 48 |
| Volume Number | 18 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2012-11-26 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Amino Acids Chemistry Beta-Lactams Chemical Synthesis Carboxylic Acids Catalysis Cyclization Hydrogenation Molecular Structure Solvents Stereoisomerism |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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