InBr 3-catalyzed cyclization of glycosides with arylamines

Pingyuan Wang; Meining Wang; Xuefeng Zhang; Guangfu Yang; Ao Zhang

doi:10.1016/j.tet.2012.04.116

InBr ₃-catalyzed cyclization of glycosides with arylamines

Pingyuan Wang
, Meining Wang
, Xuefeng Zhang
, Guangfu Yang
, Ao Zhang

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

4 Scopus citations

Abstract

Glycals have served as excellent substrates in the glycosidation reactions with arylamines to construct both C-C and C-N linkages simultaneously. However, the high reactivity and moisture/alcohol-sensitivity is also responsible for several side reactions. Herein we reported that 2,3-unsaturated glycosides can be used as alternatives of glycals to take part in the corresponding glycosidation as well. Therefore, with 10% of InBr ₃ or InI ₃ as the catalyst, 2,3-unsaturated glycosides containing various C-1 alkoxy groups reacted with arylamines smoothly and produced the glycosidation products in moderate to good yields as a pair of diastereomers with variant diastereoselectivity.

Original language	English (US)
Pages (from-to)	5386-5390
Number of pages	5
Journal	Tetrahedron
Volume	68
Issue number	27-28
DOIs	https://doi.org/10.1016/j.tet.2012.04.116
State	Published - Jul 8 2012
Externally published	Yes

Keywords

Diastereoselectivity
Glycal
Glycosidation
Glycoside
InBr

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2012.04.116

Cite this

@article{39e910f7e9b94c398829a246b5d17766,

title = "InBr 3-catalyzed cyclization of glycosides with arylamines",

abstract = "Glycals have served as excellent substrates in the glycosidation reactions with arylamines to construct both C-C and C-N linkages simultaneously. However, the high reactivity and moisture/alcohol-sensitivity is also responsible for several side reactions. Herein we reported that 2,3-unsaturated glycosides can be used as alternatives of glycals to take part in the corresponding glycosidation as well. Therefore, with 10\% of InBr 3 or InI 3 as the catalyst, 2,3-unsaturated glycosides containing various C-1 alkoxy groups reacted with arylamines smoothly and produced the glycosidation products in moderate to good yields as a pair of diastereomers with variant diastereoselectivity.",

keywords = "Diastereoselectivity, Glycal, Glycosidation, Glycoside, InBr",

author = "Pingyuan Wang and Meining Wang and Xuefeng Zhang and Guangfu Yang and Ao Zhang",

note = "Funding Information: This work was supported by grants from Chinese National Science Foundation ( 81072528 ), the Distinguished Young Scholars of Chinese NSF ( 81125021 ), National Science \& Technology Major Project on {\textquoteleft}Key New Drug Creation and Manufacturing Program{\textquoteright}, China (Numbers: 2012ZX09103-101-035 ). Support from Shanghai Commission of Science and Technology ( 10410702600 , 10JC1417100 , 10dz1910104 ) is also appreciated. ",

year = "2012",

month = jul,

day = "8",

doi = "10.1016/j.tet.2012.04.116",

language = "English (US)",

volume = "68",

pages = "5386--5390",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "27-28",

}

TY - JOUR

T1 - InBr 3-catalyzed cyclization of glycosides with arylamines

AU - Wang, Pingyuan

AU - Wang, Meining

AU - Zhang, Xuefeng

AU - Yang, Guangfu

AU - Zhang, Ao

N1 - Funding Information: This work was supported by grants from Chinese National Science Foundation ( 81072528 ), the Distinguished Young Scholars of Chinese NSF ( 81125021 ), National Science & Technology Major Project on ‘Key New Drug Creation and Manufacturing Program’, China (Numbers: 2012ZX09103-101-035 ). Support from Shanghai Commission of Science and Technology ( 10410702600 , 10JC1417100 , 10dz1910104 ) is also appreciated.

PY - 2012/7/8

Y1 - 2012/7/8

N2 - Glycals have served as excellent substrates in the glycosidation reactions with arylamines to construct both C-C and C-N linkages simultaneously. However, the high reactivity and moisture/alcohol-sensitivity is also responsible for several side reactions. Herein we reported that 2,3-unsaturated glycosides can be used as alternatives of glycals to take part in the corresponding glycosidation as well. Therefore, with 10% of InBr 3 or InI 3 as the catalyst, 2,3-unsaturated glycosides containing various C-1 alkoxy groups reacted with arylamines smoothly and produced the glycosidation products in moderate to good yields as a pair of diastereomers with variant diastereoselectivity.

AB - Glycals have served as excellent substrates in the glycosidation reactions with arylamines to construct both C-C and C-N linkages simultaneously. However, the high reactivity and moisture/alcohol-sensitivity is also responsible for several side reactions. Herein we reported that 2,3-unsaturated glycosides can be used as alternatives of glycals to take part in the corresponding glycosidation as well. Therefore, with 10% of InBr 3 or InI 3 as the catalyst, 2,3-unsaturated glycosides containing various C-1 alkoxy groups reacted with arylamines smoothly and produced the glycosidation products in moderate to good yields as a pair of diastereomers with variant diastereoselectivity.

KW - Diastereoselectivity

KW - Glycal

KW - Glycosidation

KW - Glycoside

KW - InBr

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U2 - 10.1016/j.tet.2012.04.116

DO - 10.1016/j.tet.2012.04.116

M3 - Article

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SN - 0040-4020

VL - 68

SP - 5386

EP - 5390

JO - Tetrahedron

JF - Tetrahedron

IS - 27-28

ER -