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. Author manuscript; available in PMC: 2009 Nov 12.
Published in final edited form as: J Am Chem Soc. 2008 Jun 13;130(27):8590–8591. doi: 10.1021/ja8027394

Table 1.

Catalytic Asymmetric C-H Diamination of Terminal Olefinsa

Entry Substrate Productb Yield (%)c ee (%)d
graphic file with name nihms95107t1.jpg graphic file with name nihms95107t2.jpg
1 R = Et 50 90
2 R =nC5H11 71 91
3 R = CH2Ph 67 93e,f
4 R = i-Pr 51 94g
5 R = Ph 80 90e
6 graphic file with name nihms95107t3.jpg graphic file with name nihms95107t4.jpg 80 92
7 graphic file with name nihms95107t5.jpg graphic file with name nihms95107t6.jpg 81 90g
8 graphic file with name nihms95107t7.jpg graphic file with name nihms95107t8.jpg 69 89
9 graphic file with name nihms95107t9.jpg graphic file with name nihms95107t10.jpg 85 91
10 graphic file with name nihms95107t11.jpg graphic file with name nihms95107t12.jpg 67 92
11 graphic file with name nihms95107t13.jpg graphic file with name nihms95107t14.jpg 70 97:3h,i (dr)
12 graphic file with name nihms95107t15.jpg graphic file with name nihms95107t16.jpg 66 94:6h (dr)
a

All reactions were carried out with olefin (0.80 mmol), 2 (2.0 mmol, 2.5 equiv), Pd2(dba)3 (0.04 mmol), and ligand L2 (0.176 mmol) at 65 °C for 6 h.

b

The structures represent only proposed absolute configurations by analogy.

c

Isolated yield based on olefin.

d

The ee was determined by chiral-GC (Chiraldex B-DM column) unless otherwise stated.

e

The ee was determined by chiral HPLC (Chiralpak AD column) after the removal of t-butyl groups.

f

The (R,R) configuration was determined by comparing the optical rotation with the reported one (see ref. 9a).

g

The ee was determined by chiral-GC (Chiraldex B-DM column) after the removal of t-butyl groups.

h

The ratio was determined by achiral GC (VA-5MS column).

i

The (2R,3S,4R) configuration was determined by the X-ray structure of diamination product after the removal of TMS group.