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. Author manuscript; available in PMC: 2008 Aug 13.
Published in final edited form as: J Am Chem Soc. 2005 Dec 7;127(48):16778–16779. doi: 10.1021/ja054085l

Table 2.

Substrate Scope of the Tandem Cyclization

Entry Substrate product(s) Yield(%)a
1b graphic file with name nihms60234t1.jpg
2 		graphic file with name nihms60234t2.jpg
4 		80
2b graphic file with name nihms60234t3.jpg
8 		graphic file with name nihms60234t4.jpg
9 		76
3b graphic file with name nihms60234t5.jpg
10 		graphic file with name nihms60234t6.jpg
11 		71
4c graphic file with name nihms60234t7.jpg
12 		graphic file with name nihms60234t8.jpg
13 		60d
5c graphic file with name nihms60234t9.jpg
14 		graphic file with name nihms60234t10.jpg
15 		64d
6c graphic file with name nihms60234t11.jpg
16 		graphic file with name nihms60234t12.jpg
17 		58d
7c graphic file with name nihms60234t13.jpg
18 		graphic file with name nihms60234t14.jpg
19 		58d
a

The only product isomers detected by 1H NMR analysis of the crude material are those indicated.

b

Method A: 1 equiv PMe3, 0.05 M substrate in CF3CH2OH, 60 °C.

c

Method B: 5 equiv PMe3, 0.05 M substrate in t- AmylOH, 80 °C.

d

The MBH intermediate (c.f., 1) was isolated in 7–8% yield.