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. Author manuscript; available in PMC: 2021 Nov 8.
Published in final edited form as: Nat Catal. 2021 Feb 17;4(2):164–171. doi: 10.1038/s41929-020-00569-8

Table 1.

Reaction discovery and Condition optimization.a

graphic file with name nihms-1655657-t0005.jpg
Entry Ligand Reaction conditions (3h) Conver-sion (%) Yield(%)b 4a/4a’/4a’’/4a’’’ ee (%)c (4a)
1 L1 NaBARF (10 mol %), DCE, 60°C 95 49/8/8/15 -
2 JohnPhos NaBARF (10 mol %), DCE, 60°C 0 0 -
3 JohnPhos NaBARF (10 mol %), DCE, 60°C, 10% Et3N 0 0 -
4 (R)-L2 NaBARF (10 mol %), DCE, RT 70 55/−/−/− −93
5 (S)-L3 NaBARF (10 mol %), DCE, RT 95 77/0/<3/<3 99
6 (S)-L3 AgOTf (10 mol %), DCE, RT <10 0 -
7 (S)-L3 AgNTf2 (10 mol %), DCE, RT <10 0 -
8 (S)-L3 Ag(CH3CN)2BArF4 (10 mol %), DCE, RT 60 40/−/−/− 99
9 (S)-L3 NaBARF (10 mol %), PhCF3, RT 60 32/−/−/− 99
10 (S)-L3 NaBARF (10 mol %), THF, RT 57 33/−/−/− 99
a

All reactions were run in sealed vials without replacing the atmosphere with Ar or N2. DCE = 1,2-dichloroethane. THF = tetrahydrofuran. NaBARF = sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate. Johnphos = (2-biphenyl)di-tert-butylph -osphine

b

Isolated yields.

c

Determined by HPLC using corresponding benzyl ester.