Stereoselective glycosylation reactions with chiral auxiliaries

Jin Hwan Kim; Hai Yang; Geert Jan Boons

doi:10.1002/anie.200461745

Stereoselective glycosylation reactions with chiral auxiliaries

Jin Hwan Kim
, Hai Yang
, Geert Jan Boons^*

^*Corresponding author for this work

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

Abstract

Good neighbors: A chiral auxiliary is used for the first time to control the anomeric selectivity of glycosylation reactions. In this approach, upon treatment with an activator A⁺, neighboring-group participation pation of an (S)-ethoxycarbonylbenzyl auxiliary at C2 leads to the formation of 1,2-cis glycosides, probably via a transfused ethyloxonium ion intermediate (see scheme).

Original language	English
Pages (from-to)	947-949
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	44
Issue number	6
DOIs	https://doi.org/10.1002/anie.200461745
Publication status	Published - 2 Feb 2005
Externally published	Yes

Keywords

Anomeric control
Carbohydrates
Chiral auxiliaries
Glycosides
Glycosylation

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10.1002/anie.200461745

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abstract = "Good neighbors: A chiral auxiliary is used for the first time to control the anomeric selectivity of glycosylation reactions. In this approach, upon treatment with an activator A+, neighboring-group participation pation of an (S)-ethoxycarbonylbenzyl auxiliary at C2 leads to the formation of 1,2-cis glycosides, probably via a transfused ethyloxonium ion intermediate (see scheme).",

keywords = "Anomeric control, Carbohydrates, Chiral auxiliaries, Glycosides, Glycosylation",

author = "Kim, \{Jin Hwan\} and Hai Yang and Boons, \{Geert Jan\}",

year = "2005",

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doi = "10.1002/anie.200461745",

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T1 - Stereoselective glycosylation reactions with chiral auxiliaries

AU - Kim, Jin Hwan

AU - Yang, Hai

AU - Boons, Geert Jan

PY - 2005/2/2

Y1 - 2005/2/2

N2 - Good neighbors: A chiral auxiliary is used for the first time to control the anomeric selectivity of glycosylation reactions. In this approach, upon treatment with an activator A+, neighboring-group participation pation of an (S)-ethoxycarbonylbenzyl auxiliary at C2 leads to the formation of 1,2-cis glycosides, probably via a transfused ethyloxonium ion intermediate (see scheme).

AB - Good neighbors: A chiral auxiliary is used for the first time to control the anomeric selectivity of glycosylation reactions. In this approach, upon treatment with an activator A+, neighboring-group participation pation of an (S)-ethoxycarbonylbenzyl auxiliary at C2 leads to the formation of 1,2-cis glycosides, probably via a transfused ethyloxonium ion intermediate (see scheme).

KW - Anomeric control

KW - Carbohydrates

KW - Chiral auxiliaries

KW - Glycosides

KW - Glycosylation

UR - https://www.scopus.com/pages/publications/13744262178

U2 - 10.1002/anie.200461745

DO - 10.1002/anie.200461745

M3 - Article

C2 - 15630711

AN - SCOPUS:13744262178

SN - 1433-7851

VL - 44

SP - 947

EP - 949

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 6

ER -

Stereoselective glycosylation reactions with chiral auxiliaries

Abstract

Keywords

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