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. Author manuscript; available in PMC: 2016 Apr 17.
Published in final edited form as: J Org Chem. 2015 Apr 7;80(8):4003–4016. doi: 10.1021/acs.joc.5b00364

Table 1.

Identification of Catalysta

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entry [Cu] ligand yield (%)b ee (%)c
1 Cu(MeCN)4PF6 BnBox 49 40
2 Cu(MeCN)4BF4 BnBox 58 42
3 Cu(OAc)2 BnBox 60 21
4 CuBr BnBox 55 20
5 CuI BnBox 87 60
6 CuI PhBox 63 26
7 CuI i-PrBox 57 48
8 CuI t-BuBox 59 26
9 CuI L1 75 54
10 CuI L2 82 63
11 CuI L3 70 61
12 CuI L4 76 61
graphic file with name nihms770581t1.jpg
a

Conditions: Acetal 5a (0.12 mmol, 1.0 equiv), [Cu] (0.012 mmol, 10 mol %), L* (0.014 mmol, 12 mol %), HCCPh (6a, 0.15 mmol, 1.2 equiv), Et3N (0.15 mmol, 1.2 equiv), TMSOTf (0.12 mmol, 1.0 equiv), PhMe (0.31 M), 0 °C, 15 h.

b

Determined by 1H NMR analysis using 1,3,5-trimethoxybenzene as internal standard.

c

Determined by HPLC analysis using a chiral stationary phase.