A new method for the conversion of hexose derivatives into substituted pyrrolidines

Cedric W. Holzapfel; Renier Crous; Hendrik F. Greyling; Gerhard H. Verdoorn

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
, Gerhard H. Verdoorn

Chemical Sciences

University of Johannesburg

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

The consecutive reduction and cyclisation of O-benzoyl protected 5-O- mesylhexose 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.

Original language	English
Pages (from-to)	2801-2806
Number of pages	6
Journal	Heterocycles
Volume	51
Issue number	12
DOIs	https://doi.org/10.3987/com-99-8685
Publication status	Published - 1 Dec 1999

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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Cite this

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abstract = "The consecutive reduction and cyclisation of O-benzoyl protected 5-O- mesylhexose 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.",

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AU - Holzapfel, Cedric W.

AU - Crous, Renier

AU - Greyling, Hendrik F.

AU - Verdoorn, Gerhard H.

PY - 1999/12/1

Y1 - 1999/12/1

N2 - The consecutive reduction and cyclisation of O-benzoyl protected 5-O- mesylhexose 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.

AB - The consecutive reduction and cyclisation of O-benzoyl protected 5-O- mesylhexose 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.

UR - https://www.scopus.com/pages/publications/0033372593

U2 - 10.3987/com-99-8685

DO - 10.3987/com-99-8685

M3 - Article

AN - SCOPUS:0033372593

SN - 0385-5414

VL - 51

SP - 2801

EP - 2806

JO - Heterocycles

JF - Heterocycles

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ER -

A new method for the conversion of hexose derivatives into substituted pyrrolidines

Abstract

ASJC Scopus subject areas

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