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Cu-I/Rh-II-Catalyzed Tandem Convergent Multicomponent Reaction for the Regio- and Stereocontrolled Synthesis of gamma-Oxo-beta-amino Esters

Title
Cu-I/Rh-II-Catalyzed Tandem Convergent Multicomponent Reaction for the Regio- and Stereocontrolled Synthesis of gamma-Oxo-beta-amino Esters
Authors
Jung, Da JungJeon, Hyun JiLee, Joo HyunLee, Sang-gi
Ewha Authors
이상기
SCOPUS Author ID
이상기scopus
Issue Date
2015
Journal Title
ORGANIC LETTERS
ISSN
1523-7060JCR Link1523-7052JCR Link
Citation
vol. 17, no. 14, pp. 3498 - 3501
Publisher
AMER CHEMICAL SOC
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
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.
DOI
10.1021/acs.orglett.5b01587
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자연과학대학 > 화학·나노과학전공 > Journal papers
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