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. Author manuscript; available in PMC: 2009 Apr 14.
Published in final edited form as: Tetrahedron. 2008 Apr 14;64(4):3437–3445. doi: 10.1016/j.tet.2008.02.015

Table 1.

entrya allene alkyne yield (%) E:Zb 1,4-diene
1 graphic file with name nihms43114t1.jpg 13 87 □ 1:20 graphic file with name nihms43114t2.jpg
2 graphic file with name nihms43114t3.jpg graphic file with name nihms43114t4.jpg 66 □ 1:20 graphic file with name nihms43114t5.jpg
3 graphic file with name nihms43114t6.jpg graphic file with name nihms43114t7.jpg 48 □ 1:20 graphic file with name nihms43114t8.jpg
4 graphic file with name nihms43114t9.jpg graphic file with name nihms43114t10.jpg 62 □ 20:1 graphic file with name nihms43114t11.jpg
a

Typical reaction conditions: alkyne (1.4 eq), ClTi(Oi-Pr)3 (2.1 eq), c-C5H9MgCl (4.2 eq),PhMe (−78 to −30 °C), cool to −78 °C then add allenyl alkoxide (1 eq), (−78 to 0 °C).

b

Selectivity refers to the olefin formed from the allene coupling partner.

c

rs = 4:1.

d

rr = 2:1.