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. 2011 Aug 5;13(15):4020-3.
doi: 10.1021/ol201535b. Epub 2011 Jul 6.

Asymmetric propargylation of ketones using allenylboronates catalyzed by chiral biphenols

David S Barnett  1 , Scott E Schaus
Affiliations

Asymmetric propargylation of ketones using allenylboronates catalyzed by chiral biphenols

David S Barnett et al. Org Lett. .

Abstract

Chiral biphenols catalyze the enantioselective asymmetric propargylation of ketones using allenylboronates. The reaction uses 10 mol % of 3,3'-Br(2)-BINOL as the catalyst and allenyldioxoborolane as the nucleophile, in the absence of solvent, and under microwave irradiation to afford the homopropargylic alcohol. The reaction products are obtained in good yields (60-98%) and high enantiomeric ratios (3:1-99:1). Diastereoselective propargylations using chiral racemic allenylboronates result in good diastereoselectivities (dr >86:14) and enantioselectivities (er >92:8) under the catalytic conditions.

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Figures

Figure 1
Figure 1
Methylpropargylation diastereoselectivity.
See this image and copyright information in PMC

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