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Convenient access to sterically hindered C 2 chiral 2,2,5,5-tetraphenyltetrahydrofuran-3,4-diols: intramolecular selective 1,4-cyclocondensation of (2 R,3 R)- and (2 S,3 S)-1,1,4,4-tetraphenylbutanetetraols

Convenient access to sterically hindered C 2 chiral 2,2,5,5-tetraphenyltetrahydrofuran-3,4-diols: intramolecular selective 1,4-cyclocondensation of (2

Convenient access to sterically hindered C 2 chiral 2,2,5,5-tetraphenyltetrahydrofuran-3,4-diols: intramolecular selective 1,4-cyclocondensation of (2 R,3 R)- and (2 S,3 S)-1,1,4,4-tetraphenylbutanetetraols   (Citations: 1)
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Sterically hindered C2 chiral (3R,4R)- and (3S,4S)-2,2,5,5-tetraphenyltetrahydrofuran-3,4-diols have been conveniently prepared in a very high yield via heterogeneous intramolecular selective 1,4-cyclocondensation of (2R,3R)- and (2S,3S)-1,1,4,4-tetraphenylbutanetetraol in concentrated hydrohalic acids, respectively. Preliminary examination of additives for the Barbas–List reaction showed that in certain cases, the hindered C2 chiral tetrahydrofuran-3,4-diols were better chiral auxiliaries than enantiopure (R)- and (S)-1,1′-bi-2-naphthols.
Journal: Tetrahedron-asymmetry , vol. 20, no. 21, pp. 2474-2478, 2009
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