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. 2015 Sep 17;20(9):17041–17057. doi: 10.3390/molecules200917041

Table 2.

Stereoselective formation of dioxolane 3a.

graphic file with name molecules-20-17041-i002.jpg

Entry 1 Nu-SiMe3 Product Yield (%)
1 b graphic file with name molecules-20-17041-i003.jpg graphic file with name molecules-20-17041-i004.jpg graphic file with name molecules-20-17041-i005.jpg 15 (1.2:1) c
2 56 d
3 b graphic file with name molecules-20-17041-i006.jpg 2a graphic file with name molecules-20-17041-i007.jpg 25 (1:1.2) c
4 40 d
5 graphic file with name molecules-20-17041-i008.jpg 2a graphic file with name molecules-20-17041-i009.jpg 52 d
6 graphic file with name molecules-20-17041-i010.jpg 2a graphic file with name molecules-20-17041-i011.jpg 46 d
7 graphic file with name molecules-20-17041-i012.jpg graphic file with name molecules-20-17041-i013.jpg graphic file with name molecules-20-17041-i014.jpg 39 d
8 graphic file with name molecules-20-17041-i015.jpg 2b graphic file with name molecules-20-17041-i016.jpg 37
9 1c 2b graphic file with name molecules-20-17041-i017.jpg 29 d
10 1d 2b graphic file with name molecules-20-17041-i018.jpg 25 (8:1) c
11 1a graphic file with name molecules-20-17041-i019.jpg graphic file with name molecules-20-17041-i020.jpg 34 d
12 1b 2c graphic file with name molecules-20-17041-i021.jpg 21
13 1d 2c graphic file with name molecules-20-17041-i022.jpg 29 (7:1) c
14 1b graphic file with name molecules-20-17041-i023.jpg graphic file with name molecules-20-17041-i024.jpg 27

a Reaction was initiated at −80 °C in the presence of 1 (0.32 mmol), PhI(OAc)2 (0.40 mmol), acetic acid (0.5 mmol) and BF3·OEt2 (0.8 mmol) in CH2Cl2 (4 mL). Then, 2 (1.5 mmol) was added at −40 °C and the reaction mixture was quenched at −30 °C by the addition of water; b The reaction was quenched after warming to rt; c The value in parentheses is the diastereomeric ratio of 3 and 3′ (Inline graphic); d Diastereomer was not detected by 1H-NMR.