. Author manuscript; available in PMC: 2010 Oct 14.

Published in final edited form as: J Am Chem Soc. 2009 Oct 14;131(40):14231–14233. doi: 10.1021/ja9061823

Table 1.

Catalytic asymmetric γ addition of a carbon nucleophile to an allene: Effect of reaction parameters.


Entry	change from the “standard conditions”	ee (%)^a	yield (%)^b
1	none	93	83
2	2 instead of 1	–	<2
3	3 instead of 1	67	51
4	4 instead of 1	68	51
5	5 instead of 1	−83	47
6	(S)-MONOPHOS instead of 1	–	<2
7	(R,R)-Et-DUPHOS instead of 1	–	<2
8	(R)-BINAP instead of 1	–	<2
9	quinidine instead of 1	–	<2
10	no PhOH	74	29
11	AcOH instead of PhOH	–	<2
12	toluene instead of dioxane	94	46
13	CH₂Cl₂ instead of dioxane	92	35
14	1.5 equiv instead of 5.5 equiv of MeNO₂	94	48

All data are the average of two experiments.

A negative value for the ee signifies that the enantiomer of the illustrated product is formed preferentially.

The yield was determined by GC analysis with the aid of a calibrated internal standard.