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. Author manuscript; available in PMC: 2011 Nov 10.
Published in final edited form as: J Am Chem Soc. 2010 Nov 10;132(44):15752–15765. doi: 10.1021/ja106837b

Table 5.

Substrate Scope for Catalytic Asymmetric Selenoetherification

entry substrate producta yield,b % e.r.d
1. graphic file with name nihms247258t1.jpg
(E)-29
graphic file with name nihms247258t2.jpg
28f
97% 68.9:31.1
2. graphic file with name nihms247258t3.jpg
(E)-30
graphic file with name nihms247258t4.jpg
31
86% 74.9:25.1
3. graphic file with name nihms247258t5.jpg
(E)-36
graphic file with name nihms247258t6.jpg
37
94%
37:38 = 1.4:1c
78.8:21.2
graphic file with name nihms247258t7.jpg
38
85.1:14.9
4. graphic file with name nihms247258t8.jpg
(E)-39
graphic file with name nihms247258t9.jpg
40
86%
40:41 = 4.5:1c
82.6:17.4
graphic file with name nihms247258t10.jpg
41
83.8:16.2
5. graphic file with name nihms247258t11.jpg
(Z)-29
graphic file with name nihms247258t12.jpg
42
80% 50.9:49.1
a

Aryl = 2-nitrophenyl.

b

Reaction conditions: alkene (1.0 mmol), 34 (1.1 mmol), MsOH (1.0 equiv), 35m (0.1 mmol), CHCl3 (0.1 M), 25 °C.

c

Exo:Endo ratios determined by 1H NMR spectroscopic analysis of the crude reaction mixture.

d

Determined by CSP-SFC analysis