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. 2014 Nov 12;6(2):1219–1224. doi: 10.1039/c4sc02610a

Table 4. Diastereoselective transformations of sulfolanes with construction of quaternary carbon stereocenters a .

Inline graphic
Entry Electrophile Product Yield (%) dr ee (%)
1 b Selectfluor graphic file with name c4sc02610a-u10.jpg 92 96 : 4 94
2 b Selectfluor graphic file with name c4sc02610a-u11.jpg 89 96 : 4 84
3 NCS graphic file with name c4sc02610a-u12.jpg 92 97 : 3 93
4 MeI graphic file with name c4sc02610a-u13.jpg 91 8 : 92 93
5 d Ethyl acrylate graphic file with name c4sc02610a-u14.jpg 60 4 : 96 93

aCompound 2 was treated with 1.2 equiv. of NaH in THF at room temperature, followed by the addition of 1.1 equiv. of electrophile and the subsequent stirring of the reaction mixture for 12 h; isolated yields; the trans : cis diastereomeric ratios were determined by 1H-NMR; enantiomeric excesses were determined by chiral HPLC.

bTHF/DMF (2 : 1) used as solvent.

c[2R,3R] absolute configuration determined by anomalous-dispersion effects in X-ray diffraction measurements on a crystal.

dThe reaction was stirred for 3 h.