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Issue 38, 2012
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Substrate-controlled stereoselectivity in the Yamamoto aldol reaction

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The Yamamoto aldol reaction is a vinylogous aldol reaction that relies on bulky aluminium-based Lewis acids. These activate both the aldehyde as well as become part of the enolate moiety. The report discloses the first detailed study on the substrate-controlled Yamamoto aldol reaction in which 2,3-syn and 2,3-anti disubstituted aldehydes serve as the stereodirecting elements. The “size” of the substituent in the β-position strongly determines the facial selectivity of enolate addition to the aldehyde. Large substituents favour formation of 1,3-syn diols while slim alkynyl groups preferentially lead to 1,3-anti products.

Graphical abstract: Substrate-controlled stereoselectivity in the Yamamoto aldol reaction

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Publication details

The article was received on 20 Jun 2012, accepted on 01 Aug 2012 and first published on 02 Aug 2012

Article type: Paper
DOI: 10.1039/C2OB26185E
Citation: Org. Biomol. Chem., 2012,10, 7721-7729
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    Substrate-controlled stereoselectivity in the Yamamoto aldol reaction

    N. Schläger and A. Kirschning, Org. Biomol. Chem., 2012, 10, 7721
    DOI: 10.1039/C2OB26185E

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