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. Author manuscript; available in PMC: 2014 Mar 13.
Published in final edited form as: J Am Chem Soc. 2013 Feb 28;135(10):3796–3799. doi: 10.1021/ja400691t

Table 3.

Ruthenium catalyzed [4+2] cycloaddition of isoprene 4b with vicinally dioxygenated hydrocarbons 1a-1d, 1f, 2a-2d, 2f, and 3a-3d, 3f.a

graphic file with name nihms451182u1.jpg
Entry Cycloadduct Reactant Yield %
1 graphic file with name nihms451182t1.jpg Diol 1a 78b
Hydroxyketone 2a 75b
Dicarbonyl 3a Trace
2 graphic file with name nihms451182t2.jpg Diol 1b 60b,e
Hydroxyketone 2b 72b
Dicarbonyl 3b Trace
3 graphic file with name nihms451182t3.jpg Diol 1c 90c
Hydroxyketone 2c 98c
Dicarbonyl 3c 70d
4 graphic file with name nihms451182t4.jpg Diol 1d 84b
Hydroxyketone 2d 61b
Dicarbonyl 3d 35d,f
5 graphic file with name nihms451182t5.jpg Diol 1f 90b
Hydroxyketone 2f 68b
Dicarbonyl 3f 54d,f
a

Yields are of material isolated by silica gel chromatography.

b

PCy3 (12 mol%).

c

BIPHEP (6 mol%).

d

RuH2CO(PPh3)3 (6 mol%), BIPHEP (6 mol%).

e

150 °C.

f

HCO2H (300 mol%). See Supporting Information for further details and structural assignments.