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. Author manuscript; available in PMC: 2008 Sep 11.
Published in final edited form as: J Am Chem Soc. 2005 Dec 21;127(50):17921–17937. doi: 10.1021/ja055967n

Table 3.

Addition of alkene 65a–b to enynes 64a–g.

graphic file with name nihms63200f23.jpg
entrya alkyne alkene catalyst (mol%) solvent temp. °C product % (brsm)b branched to linear ratio
1 64a 65a 67 (10) acetone 24 66aa 31 (70) 1:0
2 64a 65a 67 (10) DMF 24 66aa 5 (73) n.d.
3 64a 65a 67 (10) DMF 55 66aa 5 (65) n.d.
4 64b 65a 67 (10) acetone 24 no reaction -
5 64c 65a 67 (10) acetone 24 66ca 45 (75) 1:0
6 64d 65a 67 (10) acetone 24 66da 26 (75) 1:2
7 64d 65a 67 (10) DMF 24 66da 36 (78) 1.8:1
8 64d 65a 67 (10) DMF 55 66da 50 (76) 1.8:1
9 64d 65a 67 (10) DMF 70 66da 56 (68) 2.7:1
10 64d 65a 68 (5) MeOH 65 66da 13 (53) 2.3:1
11 64e 65a 67 (10) acetone 24 66ea 46 (65) 1:0
12 64f 65b 67 (10) acetone 24 66fb 27 (100) n.d.
13 64f 65b 67 (100) acetone 24 66fb 10 (25) n.d.
14 64f 65b 67 (10) DMF 60 66fb no reaction -
15 64g 65b 67 (10) acetone 24 66gb 10 (40) n.d.
16c 64g 65b 67 (10) acetone 24 66gb traces -
17 64g 65b 67 (10) DMF 65 66gb no reaction -
a

All reactions were run at 0.1M for 1–4 h using a 1:1 ratio of alkene to alkyne.

b

brsm indicates the yield based on recovered alkene.

c

1 equivalent of malonic acid was added.