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Issue 8, 2011
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The intramolecular asymmetric allylation of aldehydes via organo-SOMO catalysis: A novel approach to ring construction

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Abstract

The intramolecular asymmetric cyclization of aldehydes has been accomplished using singly occupied molecular orbital (SOMO) catalysis. Selective oxidation of chiral enamines (formed by the condensation of an aldehyde and a secondary amine catalyst) leads to the formation of a 3π-electron radical species. These chiral SOMO-activated radical cations undergo enantioselective cyclization with an array of pendent allylsilanes thus efficiently providing a new approach to the construction of five-, six- and seven-membered carbocycles and heterocycles.

Graphical abstract: The intramolecular asymmetric allylation of aldehydes via organo-SOMO catalysis: A novel approach to ring construction

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Publication details

The article was received on 22 Mar 2011, accepted on 19 Apr 2011, published on 19 May 2011 and first published online on 19 May 2011


Article type: Edge Article
DOI: 10.1039/C1SC00176K
Citation: Chem. Sci., 2011,2, 1470-1473
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    The intramolecular asymmetric allylation of aldehydes via organo-SOMO catalysis: A novel approach to ring construction

    P. V. Pham, K. Ashton and D. W. C. MacMillan, Chem. Sci., 2011, 2, 1470
    DOI: 10.1039/C1SC00176K

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