期刊
ORGANIC LETTERS
卷 17, 期 14, 页码 3498-3501出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b01587
关键词
-
资金
- Samsung Science and Technology Foundation [SSTF-BA1401-10]
The first example of a highly regio- and stereo-selective catalytic method for the three-component one-pot synthesis of highly functionalized alpha-vinylated gamma-oxo-beta-amino esters is disclosed. In this catalytic triad, the Cu-I-catalyst selectively catalyzes the, cycloaddition of the 1-alkyne and sulfonyl azide first resulting in the corresponding 1-sulfonyl-1,2,3-triazole. An a-imino Rh-II-carbene is generated from an open-chain alpha-imino diazo of the triazole, and this species reacts with gamma-hydroxy alpha,beta-unsaturated esters to form allylic (Z)-amino vinyl ethers. Rapid deconjugative [3,3]-sigmatropic rearrangement affords the alpha-vinyl gamma-oxo-beta-amino esters in high yields with high levels of diastereoselectivity.
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