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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 1.

Evaluation of reaction conditions for the Ir-catalyzed allylation.[a]

graphic file with name nihms805957u2.jpg
Entry Additive Yield [%][b] dr[c] ee [%][d]
1 - 95 2.0:1 n.d.
2 LiCl >99 1:1.1 n.d.
3 ZnCl2 72 16:1 n.d.
4 CuI 97 5.7:1 n.d.
5 CuCl 58 10:1 n.d.
6 CuBr >99 (>99) 14:1 92
7 CuCN 34 2.5:1 n.d.
8 CuOAc 52 1.5:1 n.d.
9 CuSCN 94 2.3:1 n.d.
10[e] CuBr 42 2.7:1 n.d.
11[f] CuBr >99 14:1 93
12[g] CuBr >99 12:1 95
13 CuBr2 0 - n.d.
[a]

The molar ratio of 1a/2a/3/LHMDS/additive = 2/1/0.02/2/2. The absolute configuration of 4aa was assigned by analogy.

[b]

Combined yield of two diastereoisomers. Determined by 1H NMR analysis with mesitylene as internal standard. The yield in parentheses is an isolated yield of two diastereoisomers.

[c]

Determined by 1H NMR analysis of crude reaction mixtures.

[d]

Determined by chiral SFC analysis of the major isomer.

[e]

KHMDS was used as the base instead of LHMDS.

[f]

1 equiv of CuBr was used.

[g]

0.5 equiv of CuBr was used.

n.d. = not determined.