Effect of oxime substituents on 9-fluorenyl carbocations

The first Sc(OTf)-catalyzed dehydration of 2-hydroxy oxime ethers to generate benzylic stabilized 1-azaallyl cations, which are captured by 1,3-carbonyls, is described. A subsequent addition of primary amines in a sequential three-component reaction affords highly substituted and densely functionalized tetrahydroindeno[2,1- b]pyrroles as single diastereomers with up to quantitative yield. Thus, three new σ-bonds and two vicinal quaternary stereogenic centers are generated in a one-pot operation.

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α-Hydroxy Ketone Precursors Leading to a Novel Class of Electro-optic Acceptors

Leslie

Sinicropi

2002

Chem. Mater.

142

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A facile high-yield synthetic route has been established for the synthesis of R-hydroxy methyl ketones. These intermediates are important precursors to the tricyanovinyldihydrofuran type of acceptor used in high µβ nonlinear optical chromophores. 3-Hydroxy-3-methyl-2-butanone is one of only three commercially available precursors of this type, limiting the chemist from making systematic studies of structure property relationships. This very general synthetic method allows a wide variety of R-hydroxy ketone structures to be easily made.Supporting Information Available: General experimental data: GC/MS analyses of compounds 1-12 and the HPLC analyses of compounds 14-23 (PDF). This material is available free of charge via the Internet at http://pubs.acs.org. CM011734T

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Effect of oxime substituents on 9-fluorenyl carbocations

Cited by 8 publications

References 17 publications

Pd(0)–polyethyleneimine complex as a partial hydrogenation catalyst of alkynes to alkenes

Pd(0)–polyethyleneimine complex as a partial hydrogenation catalyst of alkynes to alkenes

Rapid Construction of Complex 2-Pyrrolines through Lewis Acid-Catalyzed, Sequential Three-Component Reactions via in Situ-Generated 1-Azaallyl Cations

α-Hydroxy Ketone Precursors Leading to a Novel Class of Electro-optic Acceptors

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