Skip to main content
. Author manuscript; available in PMC: 2010 Sep 1.
Published in final edited form as: Nat Chem. 2010 Mar;2(3):192–196. doi: 10.1038/nchem.518

Table 1.

Enantioselective decarboxylative enolate alkylation cascadea.

graphic file with name nihms190945t1.jpg

Entry Substrate Product Time Yieldb dr(3:4)c ee(3) ee(4)
1 graphic file with name nihms190945t2.jpg graphic file with name nihms190945t3.jpg 24 h 99% 1 : 6.1 77% 87%
2 graphic file with name nihms190945t4.jpg graphic file with name nihms190945t5.jpg 48 h 91% 1 : 3.5 95% 99%
3d 72 h 88% 1 : 3.4 88% 97%
4 graphic file with name nihms190945t6.jpg graphic file with name nihms190945t7.jpg 40 h 49% 1 : 1.9 85% 88%
5e 65 h 65% 1 : 1.9 93% 94%
6 graphic file with name nihms190945t8.jpg graphic file with name nihms190945t9.jpg 24 h 56% 1 : 3.3 82% 89%
7f graphic file with name nihms190945t10.jpg graphic file with name nihms190945t11.jpg 24 h 56% 1 : 1.3 69% 70%
8g graphic file with name nihms190945t12.jpg graphic file with name nihms190945t13.jpg 72 h 57% 1 : 2.4 75% 81%
9 graphic file with name nihms190945t14.jpg graphic file with name nihms190945t15.jpg 20 h 97% 1 : > 20 - 89%
10 graphic file with name nihms190945t16.jpg graphic file with name nihms190945t17.jpg 48 h 99% 1 : > 20 71% 97%
a

General reaction conditions: 1 (0.3–0.5 mmol), 2 (1.0 equiv), [Pd2(dba)3] (5 mol%), L2 (12.5 mol%), 1,4-dioxane (0.1 M), 40 °C.

b

Combined isolated yield.

c

Determined by 1H nmr.

d

Carried out on 1 mmol scale with 2.5 mol% [Pd2(dba)3] and 6.25 mol% L2.

e

Reaction performed at 23 °C.

f

Pd(pmdba)2 (10 mol%) was used as precatalyst.

g

Reaction performed at 60 °C.