. Author manuscript; available in PMC: 2011 Apr 7.

Published in final edited form as: J Am Chem Soc. 2010 Apr 7;132(13):4568–4569. doi: 10.1021/ja101251d

Table 1.

Effect of Reaction Parameters on the Catalytic Asymmetric γ Addition of Thiols to Allenoates.


entry	change from the “standard conditions”	yield (%)^a	ee (%)
1	no (+)-1 and no 2	0^b	–
2	none	89	92
3	no 2	<5	–
4	PhOH instead of 2	<5	–
5	(S)-3 instead of (+)-1	<5	–
6	(S)-4 instead of (+)-1	81	80
7	1.1, instead of 3, equiv of thiol	80	92

All data are the average of two experiments.

The yield of the γ-addition product was determined by ¹H NMR analysis with dibromomethane as an internal standard.

Addition occurs predominantly at the β position.