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Synfacts 2007(4): 0397-0397
DOI: 10.1055/s-2007-968343
DOI: 10.1055/s-2007-968343
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Hydroxyalkylation of Homoallylsulfoximines with α-Hetero Aldehydes
A. Rajender, H.-J. Gais*
RWTH Aachen, Germany
Further Information
Publication History
Publication Date:
23 March 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200704/lookinside/thumbnails/10.1055-s-2007-968343-1.jpg)
Significance
The titanium allylation of functionalized aldehydes led to a rapid increase in complexity of the coupled partners. The method provided highly functionalized homoallylic alcohols 3 or 6, which could be further transformed in two steps into synthetically interesting products 7-11. The chiral sulfoximine moiety completely controls the stereoselectivity of the reaction, as demonstrated by reacting the two enantiomers of 5, which gave products with the same absolute stereochemistry at the alcohol and R2 in 6.