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. Author manuscript; available in PMC: 2010 Apr 17.
Published in final edited form as: J Org Chem. 2009 Apr 17;74(8):3066–3072. doi: 10.1021/jo900198b

Table 2.

Oxidation of Hydrovinylation Products. Synthesis of 2-Arylpropionic Acidsa

entry alkene product yieldb ee(%)c/oxidation method
RuCl3, NalO4 O3, NaClO2 KMnO4, NalO4
1. 2 graphic file with name nihms104939t7.jpg 96 98 78 96/ozone
2. 3 graphic file with name nihms104939t8.jpg 91 95 68 97/ozone
3. 4 graphic file with name nihms104939t9.jpg 59 --d 67 99e/RuCl3
4. 5 graphic file with name nihms104939t10.jpg 91 --d 40 97/RuCl3
5. 6 graphic file with name nihms104939t11.jpg --d 79 93 91/KMnO4
6. 7 graphic file with name nihms104939t12.jpg 84 -- -- 97/RuCl3
a

See experimental section for details.

b

Yields determined by isolated mass after column chromatography.

c

Determined by GC.

d

decomposition of starting alkene.

e

Enantiomeric excess assigned by comparison to literature rotation (ref. 21)