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Synfacts 2006(10): 1027-1027  
DOI: 10.1055/s-2006-949283
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Homopropargylic Alcohols

Contributor(s): Mark Lautens, Yann Béthuel
U. Groth*, C. Kesenheimer, J. Neidhöfer
Universität Konstanz, Germany
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Publikationsdatum:
21. September 2006 (online)

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Significance

Allenic anions display a complex behavior towards carbonyl compounds due to the equilibrium existing between the allenic and propargylic forms making the formation of two regio­isomers possible. However, in the present article, the authors successfully controlled this reactivity by using organocerium derivatives. Various aromatic and aliphatic aldehydes were transformed into homopropargylic alcohols with high regioselectivity and good to excellent diastereoselectivity.