The Journal of Organic Chemistry

Asymmetric cyclopropanation of allylic ethers: cleavage and regeneration of the chiral auxiliary

AB Charette, B Cote

文献索引：Charette, Andre B.; Cote, Bernard Journal of Organic Chemistry, 1993 , vol. 58, # 4 p. 933 - 936

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被引用次数: 47

摘要

The ring contraction reaction of 2-0-[[(trifluoromethyl) sulfonylloxyl-~-~-glucopyranosides and their corresponding a-anomers is reported. The rearrangement was shown to occur under extremely mild basic conditions to allow isolation of acid-sensitive optically active substituted cyclopropylmethanols. The chiral auxiliary can be regenerated by converting the C-glucofuranoside, byproduct of the rearrangement, into tri-0-benzyl-D-glucal (two steps).