Skip to main content
. Author manuscript; available in PMC: 2013 Jul 18.
Published in final edited form as: J Am Chem Soc. 2012 Jul 10;134(28):11400–11403. doi: 10.1021/ja305076b

Table 2.

Enantioselective SOMO-Cycloaddition: Styrene Scopea,b

graphic file with name nihms392768u2.jpg
1 graphic file with name nihms392768t1.jpg
72% yield, 9:1 dr, 93% ee
2 graphic file with name nihms392768t2.jpg
71% yield, 7:1 dr, 91% ee
3 graphic file with name nihms392768t3.jpg
76% yield, 8:1 dr, 93% ee
4 graphic file with name nihms392768t4.jpg
73% yield, 8:1 dr, 92% ee
5 graphic file with name nihms392768t5.jpg
76% yield, 3:1 dr, 94% ee
6 graphic file with name nihms392768t6.jpg
75% yield, 10:1 dr, 89% ee
7 graphic file with name nihms392768t7.jpg
61% yield, 5:1 dr, 89% ee
8 graphic file with name nihms392768t8.jpg
81% yield, 8:1 dr, 91% ee
9c graphic file with name nihms392768t9.jpg
67% yield, 3:1 dr, 92% ee
10c graphic file with name nihms392768t10.jpg
50% yield, >20:1 dr, 96% ee
a

Results listed as product, yield, diastereomeric ratio (dr), enantiomeric excess (% ee).

b

Diastereomeric ratio, % ee determined as in Table 1.

c

Reaction conducted at −20 °C using THF and Fe(phen)3(PF6)3.