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Synfacts 2010(5): 0571-0571
DOI: 10.1055/s-0029-1219696
DOI: 10.1055/s-0029-1219696
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Iridium-Catalyzed Asymmetric Alkoxy-allylation of Aldehydes
S. B. Han, H. Han, M. J. Krische*
University of Texas at Austin, USA
Further Information
Publication History
Publication Date:
22 April 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201005/lookinside/thumbnails/10.1055-s-0029-1219696-1.jpg)
Significance
There are numerous highly enantioselective methods for the allylation of aldehydes. If the allylating agent is appropriately substituted, vicinal stereocenters can be generated. One such highly desirable transformation is the addition of alkoxyallyl nucleophiles to create synthetically useful vicinal diols. Few such examples exist in the literature, and all thus far require a stoichiometric amount of allylmetal reagents. Moreover, these reactions are limited to syn-addition products. The authors present the first example of a catalytic enantioselective anti-α-alkoxyallylation. An iridium-SEGPHOS catalyst is used, and readily available acrolein gem-dibenzoate serves as the inexpensive allyl source.