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. Author manuscript; available in PMC: 2009 Dec 17.
Published in final edited form as: J Am Chem Soc. 2008 Dec 17;130(50):16870–16872. doi: 10.1021/ja8074242

Table 2.

graphic file with name nihms91435f8.jpg
entry allylic alcohol vinylsilane yield (%)a (Z:E) product
1 graphic file with name nihms91435t7.jpg
14 		20 51 ≥ 20:1 graphic file with name nihms91435t8.jpg
26
2 graphic file with name nihms91435t9.jpg
16 		20 58 ≥ 20:1 graphic file with name nihms91435t10.jpg
27
3 graphic file with name nihms91435t11.jpg
28 		20 69 ≥ 20:1 graphic file with name nihms91435t12.jpg
29
4 graphic file with name nihms91435t13.jpg
30 		20 56 ≥ 20:1 graphic file with name nihms91435t14.jpg
31
5 graphic file with name nihms91435t15.jpg
3211 		20 64 ≥ 20:1 graphic file with name nihms91435t16.jpg
33
graphic file with name nihms91435t17.jpg graphic file with name nihms91435t18.jpg
6 34; R = TBS11 20 66 ≥ 20:1 37; R = H
7 35; R = TBDPS11 20 61 ≥ 20:1 37; R = H
8 36; R = PMB11 20 61 1.2:112 38; R = PMB
a

Yield reported is over the two-step process: 1) Reductive cross-coupling (20, ClTi(Oi-Pr)3, c-C5H9MgCl, Et2O (−78 to −50 °C), then cool to −78 °C and add lithium alkoxide of the allylic alcohol (−78 to 0 °C) then, HCl (1N)), 2) oxidation (t-BuOOH, CsOH·H2O, TBAF, DMF, 70 °C).