ChemInform Abstract: Highly Enantioselective Construction of the Key Azetidin-2-ones for the Synthesis of Carbapenem Antibiotics via Intramolecular C—H Insertion Reactions of α-Methoxycarbonyl-α-diazoacetamides Catalyzed by Chiral Dirhodium(II) Carboxylates.
✍ Scribed by M. ANADA; N. WATANABE; S. HASHIMOTO
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 42 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Highly Enantioselective Construction of the Key Azetidin-2-ones for the Synthesis of Carbapenem Antibiotics via Intramolecular C-H Insertion Reactions of α-Methoxycarbonyl-α-diazoacetamides Catalyzed by Chiral Dirhodium(II) Carboxylates.
-The title reaction of compounds (I) and (III) to afford bicyclic products (II) and (IV) with enantiomeric excesses up to 96% provides a new, efficient and general method for the catalytic asymmetric synthesis of carbapenems. Other chiral rhodium-complexes are tested in the example reaction of reactant (Ia), yielding product (IIa) with 90-93% enantiomeric excesses. Starting from (IV) the pivotal intermediate (IX) for the synthesis of 1β-methylcarbapenems is prepared.