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. Author manuscript; available in PMC: 2013 Mar 21.
Published in final edited form as: J Am Chem Soc. 2012 Mar 5;134(11):5131–5137. doi: 10.1021/ja209390d

Table 1.

Catalytic asymmetric synthesis of pyrroloindolines.

graphic file with name nihms361777u1.jpg
entry ee (%)a (exo/endo)b
1) graphic file with name nihms361777t1.jpg
3a
86% yield
dr = 4:1
94/91
2) graphic file with name nihms361777t2.jpg
3b
93% yield
dr = 3:1
93/92
3) graphic file with name nihms361777t3.jpg
3c
61% yield
dr = 3:1
93/90
4) graphic file with name nihms361777t4.jpg
3d
84% yield
dr = 5:1
94/91
5) graphic file with name nihms361777t5.jpg
3e
91% yield
dr = 4:1
94/90
6) graphic file with name nihms361777t6.jpg
3f
54% yield
dr = 6:1
92/90
7) graphic file with name nihms361777t7.jpg
3g
80% yieldc
dr = 4:1
92/90
8) graphic file with name nihms361777t8.jpg
3h
65% yield
dr = >18:1
86
9) graphic file with name nihms361777t9.jpg
3i
90% yieldc
dr = 3:1
93/90
10) graphic file with name nihms361777t10.jpg
3j
18% yield
dr = 8:1
95/93
a

Determined by chiral stationary phase SFC or HPLC.

b

Determined by 1H NMR analysis of mixture.

c

1.6 equiv SnCl4 were employed.