Conversion of racemic allylic hydroperoxides into corresponding chiral 1/2,3-triols by using catalytic OsO4 and chiral cinchona ligands in the absence of co-oxidant
For the first time, removal of oxygen atoms from allylic hydroperoxide functionality and reintroduction to the double bond was achieved using catalytic OsO4 and chiral cinchona alkaloid derivatives in an acetone-water mixture to give corresponding chiral 1/2,3-triol with an enantioselectivity up to 99% ee. The hydroperoxide group was used as both a co-oxidant and a source of hydroxyl groups. This protocol is thought to have potential to provide opportunities for chiral synthesis of 1/2,3-triols from corresponding allylic hydroperoxides in the absence of co-oxidant in one stage for the first time in the literature.
G?ksu, Haydar,Gültekin, Mehmet Serdar
p. 824 - 834
(2015/08/06)
Highly stereoselective synthesis of a seven-membered carbasugar via triisobutylaluminium promoted Claisen rearrangement
2-Methylene-5-vinyl-tetrahydrofuran derivative 6 was obtained from α-D-glucose. Treatment of 6 with triisobutylaluminium (TIBAL) induced Claisen expansion reaction to give the seven-membered carbasugar derivative 7, which represents a new type of chiral b
Jia, Cai,Zhang, Yongmin,Zhang, Lihe
p. 2195 - 2199
(2007/10/03)
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