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. Author manuscript; available in PMC: 2017 May 4.
Published in final edited form as: Angew Chem Int Ed Engl. 2016 Apr 1;55(19):5819–5823. doi: 10.1002/anie.201600235

Table 3.

Ir-catalyzed allylation of acyclic α-alkoxy ketone enolates: scope of ketones.[a]

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[a]

The molar ratio of 1/2/3/LHMDS/CuBr = 2/1/0.02/2/2. The absolute configurations were assigned by analogy. The yields were reported as the combined yields of two diastereoisomers. The diastereomeric ratios were determined by 1H NMR analysis of crude reaction mixtures. The enantiomeric excesses were determined by chiral SFC analysis of major isomers.

[b]

4 mol% of 3 was used.

[c]

1 equiv of CuBr was used.

[d]

0.5 equiv of CuBr was used.

[e]

cinnamyl acetate was used instead of cinnamyl carbonate, and the reaction time was elongated to 36 h. The yield was reported as the isolated yield of the major diastereomer.