. Author manuscript; available in PMC: 2010 Apr 26.

Published in final edited form as: Org Lett. 2009 Jan 1;11(1):5–8. doi: 10.1021/ol802122p

Table 1.

Asymmetric Dihydroxylation of the C25-olefin

graphic file with name nihms-91469-t0002.jpg

substrate	X	Y	C14-15	ligand	product	25R:25S
13a	OAc	OBz	14α-H	(DHQ)₂PHAL	14a	5:1
13b	OAc	OBz	14α-H	(DHQD)₂PHAL	14b	1:3
13c	OBz	H	14α-H	(DHQ)₂PHAL	14c	1:1
13d	OBz	H	14α-H	(DHQD)₂PHAL	14d	1:1
13e	OBz	H	Δ ¹⁴	(DHQ)₂PHAL	14e	1:5
13f	OBz	H	Δ ¹⁴	(DHQD)₂PHAL	14f	2:1

^aOsO₄ (2 mol %), ligand (10 mol %), K₃Fe(CN)₆ (3 equiv), K₂CO₃ (3 equiv), t-BuOH/H₂O (1:1), 0 °C.