. Author manuscript; available in PMC: 2012 Aug 10.

Published in final edited form as: J Am Chem Soc. 2011 Jul 15;133(31):11936–11939. doi: 10.1021/ja205107x

Table 1.

Optimization Studies for Enantioselective Allylation of Phenylacetic Acid with (R)-2

entry	reaction conditions^a	ee (%)	conversion (%)
1	n-BuLi (4.0 equiv), (R)-2 (0.8 equiv)	67	68
2	n-BuLi (4.0 equiv), (R)-2 (0.9 equiv)	67	88
3	n-BuLi (4.0 equiv), (R)-2 (1.03 equiv)	93	91
4	n-BuLi (4.0 equiv), (R)-2 (1.10 equiv)	80–95	85–95
5	n-BuLi (4.0 equiv), (R)-2 (2.05 equiv)	75	89
6	n-BuLi (2.0 equiv), (R)-2 (1.05 equiv)	0	88
7	n-BuLi (4.0 equiv), (R)-2 (1.10 equiv)^b	57	77
8	n-BuLi (4.0 equiv), (R)-2 (1.10 equiv), n-BuOLi (1.0 equiv)	52	48
9	n-BuLi (4.0 equiv), (R)-2 (1.10 equiv), LiBr (1.0 equiv)	9	23

n-BuLi, PhCH₂CO₂H (0.70 mmol), and (R)-2 were combined at 0 °C in THF. After 15 min, allyl bromide was added at −78 °C over 10 min.

See the Supporting Information for additional experimental details.

Deprotonation with n-BuLi was carried out at −78 °C, not 0 °C.