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. 2010 Jun 14;107(48):20630–20635. doi: 10.1073/pnas.0914523107

Table 1.

One-pot synthesis of allylic alcohols using an organocatalytic epoxidation-Wharton sequence graphic file with name pnas.0914523107figX1.jpg

Entry Enone (1) Product (4) Yield (%)* ee (%)
1 1a graphic file with name pnas.0914523107figX2.jpg 4a graphic file with name pnas.0914523107figX3.jpg 50 (32)§ 93 (93)§
2 1b graphic file with name pnas.0914523107figX4.jpg 4b graphic file with name pnas.0914523107figX5.jpg 45 92
3 1c graphic file with name pnas.0914523107figX6.jpg 4c graphic file with name pnas.0914523107figX7.jpg 58 87
4 1d graphic file with name pnas.0914523107figX8.jpg 4d graphic file with name pnas.0914523107figX9.jpg 47 94
5 1e graphic file with name pnas.0914523107figX10.jpg 4e graphic file with name pnas.0914523107figX11.jpg 40 (35)§ 94 (94)§
6 1f graphic file with name pnas.0914523107figX12.jpg 4f graphic file with name pnas.0914523107figX13.jpg 40 98
7 1g graphic file with name pnas.0914523107figX14.jpg 4g graphic file with name pnas.0914523107figX15.jpg 45 99
8 1g graphic file with name pnas.0914523107figX16.jpg ent-4g graphic file with name pnas.0914523107figX17.jpg 42 96
9 1h graphic file with name pnas.0914523107figX18.jpg 4h graphic file with name pnas.0914523107figX19.jpg 54 96

*Yields of isolated products.

Determined by chiral stationary phase GC or HPLC.

The quasienantiomer of the catalyst is used (2b, see Scheme 5).

§Results for the sequence performed in two separate steps.