. Author manuscript; available in PMC: 2011 Aug 18.

Published in final edited form as: J Am Chem Soc. 2010 Aug 18;132(32):11027–11029. doi: 10.1021/ja105148g

Table 1.

Effect of Some Reaction Parameters on the Asymmetric Suzuki Arylation of a Racemic α-Chloroamide.


entry	variation from the “standard” conditions	ee (%)	yield (%)^a
1	none	92	89
2	no NiBr₂·glyme	–	<2
3	no (S,S)-1	–	8
4	no i-BuOH	–	8
5	water, instead of i-BuOH	91	25
6	(S,S)-2, instead of (S,S)-1	85	74
7	r.t.	82	84
8	4% NiBr₂· glyme, 5% (S,S)-1	91	78
9	X = NBnPh	–	6
10	X = NPh₂	–	4
11	X = NEt₂	76	19
12	X = NMe(OMe)	<5	84
13	X = NHMe	26	82
14	X = OEt	50	74

All data are the average of two experiments.

The yield was determined by GC or ¹H NMR analysis versus an internal standard.