Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 44, Pages 15550-15552Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja1081603
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Funding
- JSPS.KAKENHI [20245022]
- MEXT
- Grants-in-Aid for Scientific Research [20245022] Funding Source: KAKEN
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A chiral copper(II) complex of 3-(2-naphthyl)-L-alanine amide successfully catalyzes the enantioselective 1,3-dipolar cycloaddition reaction of nitrones with propioloylpyrazole and acryloylpyrazole derivatives. The asymmetric environment created by intramolecular pi-cation interaction gives the corresponding adducts in high yields with excellent enantioselectivity. This is the first successful method for the catalytic enantioselective 1,3-dipolar cycloaddition of nitrones with acetylene derivatives. The 1,3-dipolar cycloadducts can be stereoselectively converted to beta-lactams via reductive cleavage of the N-O bond using SmI2.
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