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Synfacts 2007(4): 0405-0405  
DOI: 10.1055/s-2007-968344
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cr(III)-Mediated Enantioselective Allenylation of Aldehydes

Contributor(s): Mark Lautens, Frédéric Ménard
G. Xia, H. Yamamoto*
The University of Chicago, USA
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Publication History

Publication Date:
23 March 2007 (online)

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Significance

The bis(8-quinolinolato) (TBOx) chromium complex 4 catalyzed the allenylation of a wide range of aldehydes with the highest enantio­selectivities reported to date for a catalytic system. Commercially available reacting partners 1 and 2 are used to prepare the chiral α-allenic alcohols 3. Noteworthy, the reaction constitutes the first allenylation of aldehydes where the propargyl moiety can bear an alkyl group (1, R1 = alkyl) to yield substituted allenes (3f,g).