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Synfacts 2010(6): 0718-0718
DOI: 10.1055/s-0029-1219996
DOI: 10.1055/s-0029-1219996
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Lewis Acid Assisted Triple-Aldol Cascades
B. J. Albert, H. Yamamoto*
The University of Chicago, USA
Further Information
Publication History
Publication Date:
20 May 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201006/lookinside/thumbnails/10.1055-s-0029-1219996-1.jpg)
Significance
The authors report the triflimide-catalyzed aldolization of simple aldehydes with acetaldehyde-derived super silyl enolate. Under carefully optimized reaction conditions including organoiodide additives, such as phenyl iodide or iodophenylacetylene, the reaction was driven to follow a triple-cascade pathway. The obtained products, all-syn-configured protected 1,3,5-triols, were obtained in high yields. The very exclusive diastereoselectivity was governed by the use of the super silyl protecting group, thus delivering high steric bulk for 1,3-stereocontrol.