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. Author manuscript; available in PMC: 2014 Aug 5.
Published in final edited form as: Angew Chem Int Ed Engl. 2013 Jul 5;52(32):10.1002/anie.201303552. doi: 10.1002/anie.201303552

Table 2.

Ruthenium catalyzed hydrohydroxyalkylation of styrenes 2g-2r and 3-hydroxy-2-oxindole 1a.a

graphic file with name nihms-523176-f0010.jpg
entry olefin product Ar moiety branched:linear yield (dr)
1 2g 3g (x-ray) Ph >20:1 94% (>20:1)
2 2h 3h 2-napthyl 13:1 81% (>20:1)
3 2i 3i 4-Me-Ph >20:1 83% (>20:1)
4 2j 3j 4-OMe-Ph >20:1 77% (>20:1)
5 2k 3k 2-OMe-Ph 1.3:1 91% (>20:1)
6 2l 3l 4-NMe2-Ph >20:1 65% (>20:1)
7 2m 3m 1,3-benzodioxole >20:1 81% (>20:1)
8 2n 3n 4-CI-Ph >20:1 82% (>20:1)
9 2o 3o 4-CF3-Ph >20:1 81% (>20:1)
10 2p 3p 4-CN-Ph 8.5:1 76% (>20:1)
11 2q 3q 4-CO2Me-Ph 4:1 87% (>20:1)
12 2r 3r 2-Thienyl >20:1 87% (>20:1)
a

Yields are of material isolated by silica gel chromatography. C10H15CO2H refers to 1-adamantanecarboxylic acid. See Supporting Information for further details.