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. Author manuscript; available in PMC: 2008 Aug 13.
Published in final edited form as: J Org Chem. 2006 Sep 29;71(20):7741–7746. doi: 10.1021/jo061200h

Table 1.

Asymmetric dihydroxylation of (E,E)-dienoates

graphic file with name nihms-61322-t0005.jpg
Entry R Ligand Yield(%) e.ea(11) Ratiob(11:12)
a CH2iPr (DHQ)2PHAL 82 86 (1:1)
    DHQ-4-Me-2-Quin 75 73 (>99:1)
b iPr (DHQ)2PHAL 88 60 (1.6:1)
    DHQ-4-Me-2-Quin 60c 80 (16:1)
c Ph (DHQ)2PHAL 77 —d (1:2.5)
(DHQD)2PHAL 78 —d (1:2.5)
    DHQ-4-Me-2-Quine 60 90 (>99:1)
d Me (DHQ)2PHAL 65 96 (>99:1)
(DHQD)2PHAL 68 99 (>99:1)
6a (CH2)2OTBS (DHQ)2PHAL 68 (7a) 94 (>99:1)
(DHQD)2PHAL 70 98 (>99:1)
6b (CH2)2OBn (DHQ)2PHAL 71 (7b) 97 (>99:1)
(DHQD)2PHAL 73 99 (>99:1)
a

determined by chiral HPLC

b

determined by 1H NMR

c

three eq NaHCO3 used as buffer

d

e.e. of minor isomer not determined

e

2% Os, 10% ligand