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. Author manuscript; available in PMC: 2007 May 14.
Published in final edited form as: J Am Chem Soc. 2006 Jul 26;128(29):9302–9303. doi: 10.1021/ja062637

Table 2.

Oppenauer Oxidation/Brook Rearrangement/Aldolization Reactionsa

graphic file with name nihms16459f7.jpg

entry alcohol product yield (%)b d.r.c
1d Me2CHCH2OH graphic file with name nihms16459t1.jpg 97 10:1
2d Me(CH2)5OH graphic file with name nihms16459t2.jpg 86 7:1
3d TMS(CH2)3OH graphic file with name nihms16459t3.jpg 88 5:1
4 CH2=CH(CH2)4OH graphic file with name nihms16459t4.jpg 63 5:1
5 PhCH2OH graphic file with name nihms16459t5.jpg 90 1.2:1
6 4-ClPhCH2OH graphic file with name nihms16459t6.jpg 82 1:1
7 4-MeOPhCH2OH graphic file with name nihms16459t7.jpg 85 1:1
8 PhCH(OH)Me graphic file with name nihms16459t8.jpg 67 2.5:1
9 cyclohexanon graphic file with name nihms16459t9.jpg 68 n.a.
a

Alcohol (1.5 equiv), EtMgBr (2.0 equiv), 0 °C → rt; then 1 (1.0 equiv).

b

Isolated yield.

c

Determined by 1H NMR spectroscopy; the major isomer is shown.

d

Reaction solvent: 2:1 THF/CH2Cl2.