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. Author manuscript; available in PMC: 2014 Sep 9.
Published in final edited form as: Tetrahedron. 2013 May 23;69(36):7618–7626. doi: 10.1016/j.tet.2013.05.011

Table 3.

Nucleophile scope in benzoxathiole coupling.

entry substrate nucleophile product yield (%)
1 graphic file with name nihms484876t36.jpg
32
graphic file with name nihms484876t37.jpg graphic file with name nihms484876t38.jpg
33
79
2a graphic file with name nihms484876t39.jpg
32
graphic file with name nihms484876t40.jpg
23
graphic file with name nihms484876t41.jpg
35
72
dr = 3.2:1
3a graphic file with name nihms484876t42.jpg
32
graphic file with name nihms484876t43.jpg
23-(cis)
graphic file with name nihms484876t44.jpg
35′
66
dr = 1:4.6
4 graphic file with name nihms484876t45.jpg
32
graphic file with name nihms484876t46.jpg
26
graphic file with name nihms484876t47.jpg
36
55
5 graphic file with name nihms484876t48.jpg
32
graphic file with name nihms484876t49.jpg
28
graphic file with name nihms484876t50.jpg
37
65
6 graphic file with name nihms484876t51.jpg
32
graphic file with name nihms484876t52.jpg
30
7 graphic file with name nihms484876t53.jpg
38
graphic file with name nihms484876t54.jpg
30
graphic file with name nihms484876t55.jpg
39
30
a

35 and 35′ are diastereomers. The relative stereochemical orientations have not been assigned.