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. Author manuscript; available in PMC: 2019 Mar 2.
Published in final edited form as: Org Lett. 2018 Feb 20;20(5):1333–1337. doi: 10.1021/acs.orglett.8b00067

Table 1.

Ligand Screen for Asymmetric Hydrogenation of 1aa

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entry ligand er (2a)
1 (R)-MP2-Segphos 86.3:13.7
2b (R)-MP2-Segphos 57.4:42.6
3 (R)-Segphos 91.8:8.2
4 (R)-MeO-Biphep 86.4:13.6
5 (R)-Ph-Garphos 66.5:33.5
6 (R)-Synphos 89.4:10.6
7 (R)-DTBM-Segphos 77.5:22.5
8 (R)-Cyclohexyl Soniphos 84.2:15.8
9c (R)-tBuPHOX 50.2:49.8
10b,d (R)-tBuPHOX 53.2:46.8
11 Josiphos-001 54.5:45.5
12 Josiphos-003 50.2:49.8
13b (S,S)-MeO-BoQphos 99.3:0.7
graphic file with name nihms944793u3.jpg
a

Reaction conditions: a mixture of [Ir(COD)Cl]2 and ligand was stirred in a vial for 15 min in 0.75 mL THF, before addition of 25 mg 1a, 100% conv to the desired product unless specified otherwise.

b

5 mol % of I2 was added to the catalyst solution before addition of substrate.10

c

33% conv.

d

40% conv.