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. Author manuscript; available in PMC: 2013 Mar 14.
Published in final edited form as: J Am Chem Soc. 2012 Mar 2;134(10):4941–4954. doi: 10.1021/ja210981a

Table 3. Palladium-catalyzed [3+2] reactions of N-Boc iminesa.

graphic file with name nihms361505u4.jpg

entry substrate product temp (°C) % yield % ee
1 graphic file with name nihms361505t11.jpg graphic file with name nihms361505t12.jpg 45 98 87
4 84 91
2 graphic file with name nihms361505t13.jpg graphic file with name nihms361505t14.jpg 4 80 92
3 graphic file with name nihms361505t15.jpg graphic file with name nihms361505t16.jpg 4 83 86
−15 73 90
4 graphic file with name nihms361505t17.jpg graphic file with name nihms361505t18.jpg 4 94 93
5 graphic file with name nihms361505t19.jpg graphic file with name nihms361505t20.jpg 4 91 90
6 graphic file with name nihms361505t21.jpg graphic file with name nihms361505t22.jpg 4 96 91
7 graphic file with name nihms361505t23.jpg graphic file with name nihms361505t24.jpg 4 93 85
−15 94 86
8 graphic file with name nihms361505t25.jpg graphic file with name nihms361505t26.jpg 4 73 84
9 graphic file with name nihms361505t27.jpg graphic file with name nihms361505t28.jpg 4 86 84
10b graphic file with name nihms361505t29.jpg graphic file with name nihms361505t30.jpg 4 86 85
11 graphic file with name nihms361505t31.jpg graphic file with name nihms361505t32.jpg 4 71 88
−15 65 90
12 graphic file with name nihms361505t33.jpg graphic file with name nihms361505t34.jpg 4 81 83
13 graphic file with name nihms361505t35.jpg graphic file with name nihms361505t36.jpg 4 75 86
14 graphic file with name nihms361505t37.jpg graphic file with name nihms361505t38.jpg 4 71 91
15 graphic file with name nihms361505t39.jpg graphic file with name nihms361505t40.jpg 4 74 88
−15 60 90
16 graphic file with name nihms361505t41.jpg graphic file with name nihms361505t42.jpg 4 74 70
17 graphic file with name nihms361505t43.jpg graphic file with name nihms361505t44.jpg 4 88 72
18 graphic file with name nihms361505t45.jpg graphic file with name nihms361505t46.jpg 4 43 22
a

All reactions were performed at 0.2 M in toluene with 5 mol% Pd(dba)2, 10 mol% ligand, 1.6 equiv 1, and stirred for 4 hours. Yields are isolated values; ee's were determined by chiral HPLC or chiral GC.

b

Reaction performed with 2.5 mol% Pd(dba)2 and 5 mol% L12.