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. Author manuscript; available in PMC: 2010 Jul 2.
Published in final edited form as: Org Lett. 2009 Jul 2;11(13):2944–2947. doi: 10.1021/ol901151u

Table 1.

Reaction of a variety of allylic carbonates with BocNH2.

graphic file with name nihms123810t1.jpg

entrya product b:lb yield (%)c ee (%)d
1e graphic file with name nihms123810t2.jpg 94:6 85 99
2f X = CF3 81:19 65 99
3f X = Br 91:9 79 99
4 X = OMe 99:1 85 99
5 graphic file with name nihms123810t3.jpg 95:5 81 99
6 graphic file with name nihms123810t4.jpg 83:17 50 98
7 graphic file with name nihms123810t5.jpg 89:11 79 95
8 graphic file with name nihms123810t6.jpg 85:15 65 97
9 graphic file with name nihms123810t7.jpg 83:17 61 97
10f,g graphic file with name nihms123810t8.jpg 55:45 25 99
a

General conditions: 0.7 mmol BocNH2, 0.5 mmol carbonate, 0.02 mmol 1d, and 10 µL dodecane in 0.5 mL ether. Results are an average of two runs.

b

Determined by NMR analysis of the crude reaction mixture or isolation.

c

Isolated yield of branched product.

d

Determined by chiral HPLC analysis, see Supporting Information for details.

e

THF was used as solvent.

f

K3PO4 (0.25 mmol) was added.

g

Reaction was run at 30 °C.