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Synfacts 2008(11): 1189-1189  
DOI: 10.1055/s-0028-1083429
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Titanium-Catalyzed Asymmetric Alkylation of Aldehydes Using Trialkylboranes

Contributor(s): Mark Lautens, Praew Thansandote
T. Ukon, T. Harada*
Kyoto Institute of Technology, Japan
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Publikationsverlauf

Publikationsdatum:
23. Oktober 2008 (online)

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Significance

A catalytic asymmetric titanium(IV)-catalyzed alkylation of aldehydes using trialkylboranes is described. Good yields and enantioselectivities are seen for aromatic and unsaturated aldehydes, though reactions with aliphatic alde-hydes are lower-yielding and heteroaryl aldehydes give lower enantioselectivities. For the related asymmetric alkylation of aldehydes using Grignard reagents see: Y. Maramatsu, T. Harada Angew. Chem. Int. Ed. 2008, 47, 1088.