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Institute of Organic Chemistry and Center of Biomolecular Drug Research (BMWZ), Schneiderberg 1b, 30167 Hannover
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Org. Biomol. Chem., 2012,10, 7721-7729
20 Jun 2012,
01 Aug 2012
First published online
02 Aug 2012
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.
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Organic & Biomolecular Chemistry
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