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Communication | Regular issue | Vol 51, No. 12, 1999, pp.2801-2806
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8685
A New Method for the Conversion of Hexose Derivatives into Substituted Pyrrolidines

Cedric W. Holzapfel,* Renier Crous, Hendrik F. Greyling, and Gerhard H. Verdoorn

*Department o f Chemistry and Biochemistry, Rand Afrikaans University, P.O. Box 524, Auckland Park, 2006, Johanesberg, South Africa


The consecutive reduction and cyclisation of O-benzoyl protected 5-O-mesyihexose O-(tert-butyldiphenylsilyl)oximes to afford chiral N-hydroxypyrrolidines is discussed. The mechanism involves a cascade of neighboring group participation steps involving the O-benzoyl protecting groups. This protocol gave rise to new chiral N-hydroxypyrrolidines in good overall yield.