188
ORGANIC SYNTHESIS—1995
II.F.2 Hvdroxvlations
II.F.2-1 Lohray, B.B. et al., TL, 35,4209; Sharpless, K.B. et al., JACS,
116, 1278 and 8470 and TL, 35,7315.
On the Mechanism of Asymmetric Dihydroxylation (AD) of Alkenes.
II.F.2-2 Salvadori, P. et al., T, 50, 11321.
OH
R
. ^
OsQ4
R \ ^ k
~^<^
R'
polymer bound
ΊΓ
quinine derivative
HO 4Q g 9 %
13-89 % e.e.
II.F.2-3 Kuwajima, I. et al., TL, 35, 7813; Sharpless, K.B. et al., TL, 35,
3469, 4685, and 5611 and JOC, 59, 8302; Girijavallabhan, V.M. et al., SL,
263; Jung, M.E. and Gardiner, J.M., TL, 35, 6755; Bittman, R. et al., JOC,
35, 2630; Takano, S. et al., SL, 119; Takahata, H., Inose, K., and Momose,
T., H, 38, 269; Corey, E.J. et al., TL, 35, 6427 and JACS, 116, 12579;
Lohray, B.B. et al., TL, 35, 6559; Bassindale, A.R., Taylor, P.G., and Xu,
Y., JCS(Pl), 1061; Ko, S.Y. et al., JOC, 59, 2570.
OPiv
TBSO.
OsQ 4 , DHQD-PHN
K 3 F(CN) 6 , K 2 C0 3
Ό
OPiv
HO.
OHC
88%,94%e.e.
II.F.2-4 Lohray, B.B. et al., JOC, 59, 1375.
Origin of α-Hydroxy Ketones in the Osmium Tetroxide Catalyzed
Asymmetric Dihydroxylation of Alkenes.