Indium(III) Triflate-Catalyzed Glycosylation through an Ambient Activation of Glycosyl Fluoride

Jaehoon Sim; Seok Ho Kim; Joonseong Hur; Changjin Lim; Hyun Su Kim; Young Ger Suh

doi:10.1002/ajoc.201800582

Indium(III) Triflate-Catalyzed Glycosylation through an Ambient Activation of Glycosyl Fluoride

Jaehoon Sim
, Seok Ho Kim
, Joonseong Hur
, Changjin Lim
, Hyun Su Kim
, Young Ger Suh^*

^*Corresponding author for this work

Department of Pharmacy

CHA University
Seoul National University

Research output: Contribution to journal › Journal article › peer-review

10 Scopus citations

Abstract

A highly efficient catalytic glycosylation using glycosyl fluoride in the presence of a mild and non-toxic Lewis acid, indium(III) triflate, was achieved. The facile and convenient glycosylation procedure does not require pre-activation steps, pre-distillation, or cumbersome work-up process, and it was compatible with a broad range of alcohol acceptors under ambient conditions. Furthermore, the stereoselective C-glycosylation smoothly proceeded under the same conditions.

Original language	English
Pages (from-to)	107-110
Number of pages	4
Journal	Asian Journal of Organic Chemistry
Volume	8
Issue number	1
DOIs	https://doi.org/10.1002/ajoc.201800582
State	Published - 2019.01

Keywords

ambient condition
catalytic glycosylation
glycosyl fluoride
indium triflate
synthetic methods

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10.1002/ajoc.201800582

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@article{1e0edb497ed244018513ff41144617fd,

title = "Indium(III) Triflate-Catalyzed Glycosylation through an Ambient Activation of Glycosyl Fluoride",

abstract = "A highly efficient catalytic glycosylation using glycosyl fluoride in the presence of a mild and non-toxic Lewis acid, indium(III) triflate, was achieved. The facile and convenient glycosylation procedure does not require pre-activation steps, pre-distillation, or cumbersome work-up process, and it was compatible with a broad range of alcohol acceptors under ambient conditions. Furthermore, the stereoselective C-glycosylation smoothly proceeded under the same conditions.",

keywords = "ambient condition, catalytic glycosylation, glycosyl fluoride, indium triflate, synthetic methods",

author = "Jaehoon Sim and Kim, \{Seok Ho\} and Joonseong Hur and Changjin Lim and Kim, \{Hyun Su\} and Suh, \{Young Ger\}",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2019",

month = jan,

doi = "10.1002/ajoc.201800582",

language = "English",

volume = "8",

pages = "107--110",

journal = "Asian Journal of Organic Chemistry",

issn = "2193-5807",

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}

TY - JOUR

T1 - Indium(III) Triflate-Catalyzed Glycosylation through an Ambient Activation of Glycosyl Fluoride

AU - Sim, Jaehoon

AU - Kim, Seok Ho

AU - Hur, Joonseong

AU - Lim, Changjin

AU - Kim, Hyun Su

AU - Suh, Young Ger

PY - 2019/1

Y1 - 2019/1

N2 - A highly efficient catalytic glycosylation using glycosyl fluoride in the presence of a mild and non-toxic Lewis acid, indium(III) triflate, was achieved. The facile and convenient glycosylation procedure does not require pre-activation steps, pre-distillation, or cumbersome work-up process, and it was compatible with a broad range of alcohol acceptors under ambient conditions. Furthermore, the stereoselective C-glycosylation smoothly proceeded under the same conditions.

AB - A highly efficient catalytic glycosylation using glycosyl fluoride in the presence of a mild and non-toxic Lewis acid, indium(III) triflate, was achieved. The facile and convenient glycosylation procedure does not require pre-activation steps, pre-distillation, or cumbersome work-up process, and it was compatible with a broad range of alcohol acceptors under ambient conditions. Furthermore, the stereoselective C-glycosylation smoothly proceeded under the same conditions.

KW - ambient condition

KW - catalytic glycosylation

KW - glycosyl fluoride

KW - indium triflate

KW - synthetic methods

UR - https://www.scopus.com/pages/publications/85058062353

U2 - 10.1002/ajoc.201800582

DO - 10.1002/ajoc.201800582

M3 - Journal article

AN - SCOPUS:85058062353

SN - 2193-5807

VL - 8

SP - 107

EP - 110

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 1

ER -

Indium(III) Triflate-Catalyzed Glycosylation through an Ambient Activation of Glycosyl Fluoride

Abstract

Keywords

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