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Synfacts 2011(9): 0973-0973  
DOI: 10.1055/s-0030-1261010
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Alkoxyallylation of Aldehydes

Contributor(s): Mark Lautens, Lei Zhang
T. Mejuch, M. Botoshansky, I. Marek*
Technion-Israel Institute of Technology, Haifa, Israel
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Publication History

Publication Date:
19 August 2011 (online)

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Significance

E-Configured alkoxy-substituted allyl metal equivalents (A) are synthetically difficult to access. The authors report a strategy to generate these allylmetal species in situ via carbocupration of ynol ethers. Subsequent zinc homologation and trapping with aldehydes lead to the diastereoselective formation of allylic vicinal diols in a one-pot operation.