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. Author manuscript; available in PMC: 2011 Jul 21.
Published in final edited form as: J Am Chem Soc. 2010 Jul 21;132(28):9576–9578. doi: 10.1021/ja103836h

Table 1.

graphic file with name nihms218366u2.jpg
entry 1,5-diene yielda (%) path selectivityb stereoselectivity major productd
1 graphic file with name nihms218366t1.jpg
2		 - 1.4:1 1:1 graphic file with name nihms218366t2.jpg
3
2 graphic file with name nihms218366t3.jpg
4		 50 ≥ 20:1 - graphic file with name nihms218366t4.jpg
5
3 graphic file with name nihms218366t5.jpg
6		 57 ≥ 20:1 ≥ 20:1c graphic file with name nihms218366t6.jpg
7
4 graphic file with name nihms218366t7.jpg
8		 57 ≥ 20:1 ≥ 20:1c graphic file with name nihms218366t8.jpg
9
5 graphic file with name nihms218366t9.jpg
10		 76 ≥ 20:1 ≥ 20:1c graphic file with name nihms218366t10.jpg
11
6 graphic file with name nihms218366t11.jpg
12		 53e ≥ 20:1 ≥ 20:1c graphic file with name nihms218366t12.jpg
13
a

Reaction conditions: 1 (2–3 equiv.), Ti(Oi-Pr)4, c-C5H9MgCl, PhMe (−78 to −35 °C), then cool to −78 °C and add Li alkoxide of the allylic alcohol as a solution in THF (warm to 0 °C).

b

In cases where selectivity is reported as ≥20:1, no evidence was found for products derived from C–C bond formation by a different path.

c

In cases where selectivity is reported as ≥ 20:1, no evidence was found for the formation of stereoisomeric products.

d

Olefin geometry of the major products was assigned by analogy to previous examples.

e

Yield reported is after HPLC purification.