Skip to main content
. Author manuscript; available in PMC: 2012 Aug 5.
Published in final edited form as: Org Lett. 2011 Jun 28;13(15):3778–3781. doi: 10.1021/ol2010819

Table 1.

RRRM through catalytic enantioselective silylation

graphic file with name nihms-307923-f0005.jpg
entry substrate A (ee) B (ee) yield (comb.) ratio A/B
(1) graphic file with name nihms-307923-t0006.jpg graphic file with name nihms-307923-t0007.jpg graphic file with name nihms-307923-t0008.jpg 92%a 50/50
(2) graphic file with name nihms-307923-t0009.jpg graphic file with name nihms-307923-t0010.jpg graphic file with name nihms-307923-t0011.jpg 89%b 58/42
(3) graphic file with name nihms-307923-t0012.jpg graphic file with name nihms-307923-t0013.jpg graphic file with name nihms-307923-t0014.jpg 89%c 64/36
(4) graphic file with name nihms-307923-t0015.jpg graphic file with name nihms-307923-t0016.jpg graphic file with name nihms-307923-t0017.jpg 90%d 50/50
(5) graphic file with name nihms-307923-t0018.jpg graphic file with name nihms-307923-t0019.jpg graphic file with name nihms-307923-t0020.jpg 75%e 52/48
(6) graphic file with name nihms-307923-t0021.jpg graphic file with name nihms-307923-t0022.jpg graphic file with name nihms-307923-t0023.jpg 50%f 52/48

Conditions:

a

TBSCl (2 equiv), DIPEA (1 equiv), toluene [1 M], -30 °C, 120 h.

b

TBSCl (1.5 equiv), DIPEA (1 equiv), toluene [1 M], -60 °C, 120 h.

c

TBSCl (1.5 equiv), DIPEA (1 equiv), toluene [1 M], -30 °C, 120 h.

d

TESCl (1.5 equiv), DIPEA (1 equiv), THF [1 M], -60 °C, 72 h.

e

TBSCl (1 equiv), DIPEA (1 equiv), toluene [1 M], -60 °C, 120 h.

f

TBSCl (1 equiv), DIPEA (1.25 equiv), THF [1 M], -30 °C, 110 h.