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. Author manuscript; available in PMC: 2022 Sep 1.
Published in final edited form as: J Am Chem Soc. 2021 Aug 16;143(34):13759–13768. doi: 10.1021/jacs.1c05769

Table 1.

Structural Effect of Josiphos on Transformationa

graphic file with name nihms-1801038-t0007.jpg
entry R; R' yield (SM %)b ee (%)c
1 Me; H 59% (23) 45
2 Me; OMe 31% (14) 44
3 tBu; OMe 41% (<1) 70
4 Mes; H 58% (38) 75
5 TTB; H 3% (79) nd
6 TMS; H 73% (<1) 75
7 TES; H 66% (<1) 83
8 CF3; H 43% (<2) 71
9 iPr(F7); H 44% (43) 86
graphic file with name nihms-1801038-t0008.jpg
a

Standard conditions: 1a (0.10 mmol, 1.0 equiv), 2 (0.135 mmol, 1.35 equiv), CuCl (5 mol %), L (6 mol %), THF (1.0 mL), 65 °C, 24 h.

b

Yield was determined by 19F NMR of crude reaction, using PhF as an internal standard.

c

Determined by HPLC with a chiral stationary phase.