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. Author manuscript; available in PMC: 2010 Oct 29.
Published in final edited form as: Org Lett. 2008 Feb 28;10(6):1039–1042. doi: 10.1021/ol702821j

Table 3. Enantioconvergent Decarboxylative Protonationsa.

graphic file with name nihms243551u4.jpg

entry substrate product ee A (%) time (h) yield (%) ee B (%)
1 graphic file with name nihms243551t12.jpg graphic file with name nihms243551t13.jpg R = Me 88 0.5 99b 86 (R)
2 R = Et 92 0.5 99b 89 (R)
3 R = Bn 83 0.5 90 78 (S)
4 graphic file with name nihms243551t14.jpg graphic file with name nihms243551t15.jpg 91 5 87 89
5 graphic file with name nihms243551t16.jpg graphic file with name nihms243551t17.jpg 85 0.5 97 80
6 graphic file with name nihms243551t18.jpg graphic file with name nihms243551t19.jpg R = Me 90 0.5 86 77 (S)
7 R = Allyl 82 0.5 83 77 (R)
8 graphic file with name nihms243551t20.jpg graphic file with name nihms243551t21.jpg 0.5 77 77
9 graphic file with name nihms243551t22.jpg graphic file with name nihms243551t23.jpg 0.5 79 61 (S)
a

Reactions were performed on two different scales, A: 0.1 mmol of substrate, and B: 0.3 mmol of substrate, each at 0.033 M in p-dioxane. Column ee A reflects results for conditions A; time, isolated yield, and ee B are reported for conditions B. Isolated yields from conditions A were comparable to those with conditions B. The major enantiomer was the same under either set of conditions. Enantiomeric excess was measured following chromatography on silica gel; no erosion of ee was observed as a result of purification.

b

GC yield using tridecane as internal standard.