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. Author manuscript; available in PMC: 2018 Jan 25.
Published in final edited form as: J Am Chem Soc. 2017 Jan 12;139(3):1049–1052. doi: 10.1021/jacs.6b11336

Table 3.

Asymmetric Cyclopropanation of Styrene with Various Sulfonyl Hydrazones Catalyzed by [Co(P3)]a

graphic file with name nihms840891t12.jpg
entry graphic file with name nihms840891t13.jpg graphic file with name nihms840891t14.jpgb product temp.
(°C)		 yield
(%)c 		drd ee
(%)e
1 graphic file with name nihms840891t15.jpg Ts(1b) 3ba 40 78 95:5 99
2 graphic file with name nihms840891t16.jpg Ts(1f) 3fa 40 91 95:5 94
3 graphic file with name nihms840891t17.jpg Ts(1g) 3ga RT 90 94:6 86
4 Ts (1g) 3ga 0 <10 - -
5 TPS (1g') 3g'a 0 83 >99:1 93
6 graphic file with name nihms840891t18.jpg Ts (1h) 3ha RT 58 96:4 71
7 TPS (1h') 3h'a 0 75 >99:1 76
8 graphic file with name nihms840891t19.jpg Ts (1i) 3ia RT 85 96:4 88
9 TPS (1i') 3i'a 0 85 >99:1 93
10 graphic file with name nihms840891t20.jpg Ts (1j) 3ja RT 82 95:5 68
11 TPS (1j') 3j'a 0 81 >99:1 89
a

Carried out with 1x (0.1 mmol) and 2a (1.5 equiv.) in the presence of Cs2C O3 (2 equiv.) in methanol (0.6 mL).

b

Ts = 4-toluenesulfonyl; TPS = (2,4,6-triisopropyl) phenyl sulfonyl.

c

Isolated yields.

d

Determined by 1H NMR.

e

Determined by chiral HPLC for the major trans diastereomer.