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Issue 6, 2016
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Catalytic discrimination between formyl groups in regio- and stereoselective intramolecular cross-aldol reactions

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Abstract

Catalytic discrimination between inequivalent formyl groups was achieved using an aniline-type acid–base catalyst for the regio-, diastereo-, and enantioselective intramolecular cross-aldol reactions of enolizable dials. Although L-proline gave a mixture of the regio- and stereoisomeric products in the presence of an N-containing 1,6-dial, the aniline-type catalyst afforded anti-3,4-disubstituted pyrrolidine in high regio-, and stereoselectivity beyond the background reaction, which led to the regioisomeric 2,3-disubstituted products. The mild reactivity of the aniline-type amine facilitated catalytic discrimination between the inequivalent formyl groups. Kinetic isotope effect studies and reductive amination experiments suggested that the regioselectivity was controlled under the enamine-forming steps.

Graphical abstract: Catalytic discrimination between formyl groups in regio- and stereoselective intramolecular cross-aldol reactions

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Publication details

The article was received on 29 Nov 2015, accepted on 18 Feb 2016 and first published on 22 Feb 2016


Article type: Edge Article
DOI: 10.1039/C5SC04594K
Citation: Chem. Sci., 2016,7, 3791-3797
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    Catalytic discrimination between formyl groups in regio- and stereoselective intramolecular cross-aldol reactions

    T. Baba, J. Yamamoto, K. Hayashi, M. Sato, M. Yamanaka, T. Kawabata and T. Furuta, Chem. Sci., 2016, 7, 3791
    DOI: 10.1039/C5SC04594K

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