Novel one-pot synthesis of diverse gamma,delta-unsaturated beta-ketoesters by thermal cascade reactions of diazodicarbonyl compounds and enol ethers: transformation into substituted 3,5-diketoesters

Title
Novel one-pot synthesis of diverse gamma,delta-unsaturated beta-ketoesters by thermal cascade reactions of diazodicarbonyl compounds and enol ethers: transformation into substituted 3,5-diketoesters
Author(s)
이용록판딧라메쉬월프라사드
Keywords
KETO-ESTER DIANIONS; ONE-STEP SYNTHESIS; ASYMMETRIC-SYNTHESIS; RHODIUM(II)-CATALYZED REACTIONS; WOLFF REARRANGEMENT; ORGANIC-SYNTHESIS; EFFICIENT SYNTHESIS; ACID-CHLORIDES; GAMMA-PYRONES; KETENES
Issue Date
201407
Publisher
ROYAL SOC CHEMISTRY
Citation
ORGANIC & BIOMOLECULAR CHEMISTRY, v.12, no.25, pp.4407 - 4411
Abstract
Sequential Wolff rearrangement of alpha-diazo-beta-ketoesters followed by trapping of the ketene intermediates with enol ethers generated a variety of gamma,delta-unsaturated beta-ketoesters. This method involves a novel thermal cascade reaction and allows the synthesis of gamma,delta-unsaturated beta-ketoesters with trans-stereochemistry under catalyst-free conditions. The synthesized compounds were further transformed into novel 3,5-diketoesters, which were used for the synthesis of naturally occurring 2-pyrone and 1-naphthoic acid ester.
URI
http://hdl.handle.net/YU.REPOSITORY/31467http://dx.doi.org/10.1039/c4ob00664j
ISSN
1477-0520
Appears in Collections:
공과대학 > 화학공학부 > Articles
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