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. Author manuscript; available in PMC: 2009 Aug 26.
Published in final edited form as: J Am Chem Soc. 2007 Nov 16;129(49):15112–15113. doi: 10.1021/ja075678u

Table 1.

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entry allylic alcohol alkyne yield (%) 1,4-dienea
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1 6; R = H, n=1 7 65 8; n=1
2 9; R = H, n=2 68 10; n=2
3 11; R = Me, n=1 61 12; R = Me, n=1
4 13; R = Ph, n=1 79 14; R = Ph, n=1
5 15; R = c-C5H9, n=1 40 16; R = c-C5H9, n=1
6 graphic file with name nihms63560t4.jpg
17 		7 57 graphic file with name nihms63560t5.jpg
18
7b graphic file with name nihms63560t6.jpg
19(er = 97:3)		 7 54 graphic file with name nihms63560t7.jpg
20c (er = 96:4)
8 graphic file with name nihms63560t8.jpg
21 		7 50 graphic file with name nihms63560t9.jpg
22(dr ≥ 20:1)
a

Reaction conditions for cross coupling: alkyne (1.0 eq), ClTi(Oi-Pr)3, PhMe, C5H9MgCl, −78 to −35 °C, then recool to −78 °C, add Li-alkoxide of allylic alcohol (1.0 eq) (−78 to 0 °C).

b

ClTi(Oi-Pr)3 was replaced with Ti(Oi-Pr)4 in this experiment.

c

Absolute stereochemistry not determined.