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Synfacts 2010(2): 0191-0191  
DOI: 10.1055/s-0029-1219216
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Homoallenylation of Aldehydes

Contributor(s): Mark Lautens, Stephen G. Newman
V. Coeffard, M. Aylward, P. J. Guiry*
University College Dublin, Ireland
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Publication History

Publication Date:
21 January 2010 (online)

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Significance

Despite their utility, few general methods exist for the synthesis of β-allenols. The authors report the first highly enantioselective ­catalytic homoallenylation of aldehydes to access this valuable class of substrates. This Nozaki-Hiyama-Kishi (NHK) reaction achieves excellent enantioselectivity through the use of a C 1-symmetric bisoxazoline ligand previously developed and applied to allylation and crotylation reactions (P. J. Guiry and co-workers Adv. Synth. Catal. 2006, 348, 551).