Enantioselective synthesis of substituted indanones from silyloxyallenes

Jonathan A. Brekan; Troy E. Reynolds; Karl A Scheidt

doi:10.1021/ja909669e

Enantioselective synthesis of substituted indanones from silyloxyallenes

Jonathan A. Brekan, Troy E. Reynolds, Karl A Scheidt

Chemistry

Research output: Contribution to journal › Article › peer-review

38 Scopus citations

Abstract

(Chemical Equation Presented) A new approach for the synthesis of enantioenriched indanones by asymmetric carbonyl-ene/intramolecular Heck cyclization from racemic silyloxyallenes has been developed. The modular procedure affords highly substituted indenes and indanones with excellent chirality transfer from the optically active carbinols. Full transfer of stereochemical information is achieved in the presence of 1,2,2,6,6- pentamethylpiperidine and PdCl₂(PPh₃)₂ (1 mol %) in DMF under microwave heating. Short reaction times and high yields have been demonstrated on a variety of substrates.

Original language	English (US)
Pages (from-to)	1472-1473
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	132
Issue number	5
DOIs	https://doi.org/10.1021/ja909669e
State	Published - Feb 10 2010

ASJC Scopus subject areas

Chemistry(all)
Catalysis
Biochemistry
Colloid and Surface Chemistry

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AU - Reynolds, Troy E.

AU - Scheidt, Karl A

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N2 - (Chemical Equation Presented) A new approach for the synthesis of enantioenriched indanones by asymmetric carbonyl-ene/intramolecular Heck cyclization from racemic silyloxyallenes has been developed. The modular procedure affords highly substituted indenes and indanones with excellent chirality transfer from the optically active carbinols. Full transfer of stereochemical information is achieved in the presence of 1,2,2,6,6- pentamethylpiperidine and PdCl2(PPh3)2 (1 mol %) in DMF under microwave heating. Short reaction times and high yields have been demonstrated on a variety of substrates.

AB - (Chemical Equation Presented) A new approach for the synthesis of enantioenriched indanones by asymmetric carbonyl-ene/intramolecular Heck cyclization from racemic silyloxyallenes has been developed. The modular procedure affords highly substituted indenes and indanones with excellent chirality transfer from the optically active carbinols. Full transfer of stereochemical information is achieved in the presence of 1,2,2,6,6- pentamethylpiperidine and PdCl2(PPh3)2 (1 mol %) in DMF under microwave heating. Short reaction times and high yields have been demonstrated on a variety of substrates.

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Enantioselective synthesis of substituted indanones from silyloxyallenes

Abstract

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