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. 2019 Jan 15;10(8):2507–2512. doi: 10.1039/c8sc05397a

Table 2. Screening bisphosphine ligands for asymmetric hydrogenation of 2-phenylbenzo[b]thiophene 1,1-dioxide 1a a .

Inline graphic
Entry Ligand Conv. b [%] ee c [%]
1 ZhaoPhos L1 >99 >99
2 L2 >99 >99
3 L3 73 56
4 L4 NR NA
5 d ZhaoPhos L1 81 96
6 d L2 95 98

aUnless otherwise mentioned, all reactions were carried out with a [Rh(NBD)2]BF4/ligand/substrate 1a (0.1 mmol) ratio of 1 : 1.1 : 100 in 1.0 mL CF3CH2OH under 50 atm H2 at 70 °C for 40 h, and the catalyst was pre-complexed in CH2Cl2 (0.1 mL for each reaction vial).

bDetermined by 1H NMR analysis.

cThe ee value was determined by HPLC on a chiral phase.

dCatalyst loading is 0.5 mol%, 12 h. NR = no reaction, NA = not available.