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. Author manuscript; available in PMC: 2009 Dec 24.
Published in final edited form as: Tetrahedron Lett. 2009 Jun 24;50(25):3031–3034. doi: 10.1016/j.tetlet.2009.04.003

Table 1.

Wittig reaction of boronate ylide (11) with various aldehydesa

Entry Aldehyde Product Yieldb (%)
1 graphic file with name nihms161287t1.jpg graphic file with name nihms161287t2.jpg
1b E:Z= 74:26
86
2 graphic file with name nihms161287t3.jpg graphic file with name nihms161287t4.jpg
1c E:Z= 64:36
72
3 graphic file with name nihms161287t5.jpg graphic file with name nihms161287t6.jpg
1dE:Z= 75:25
71
4 graphic file with name nihms161287t7.jpg graphic file with name nihms161287t8.jpg
1e E:Z= 55:45
76
5 graphic file with name nihms161287t9.jpg graphic file with name nihms161287t10.jpg
1f E:Z= 100:0
78
a

All reactions were performed using 1 equiv of aldehyde and 3 equiv of tBuONa in DMF for 2–12 h.

b

Isolated yield (mixture of E and Z) refers to aldehyde and the E/Z ratios were determined by 1H NMR.