C4-symmetric alkoxyresorcin[4]arene triflates: The use of palladium-catalyzed reactions in the synthesis of axially chiral derivatives with amino- and/or alkoxy-substituents

Philip C. Bulman Page; Terence R. Bygrave; Yohan Chan; Harry Heaney; Vickie McKee

doi:10.1002/ejoc.201100122

C4-symmetric alkoxyresorcin[4]arene triflates: The use of palladium-catalyzed reactions in the synthesis of axially chiral derivatives with amino- and/or alkoxy-substituents

Philip C. Bulman Page, Terence R. Bygrave, Yohan Chan, Harry Heaney, Vickie McKee

Chemistry of Materials and Catalysis

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

7 Citations (Scopus)

Abstract

The conversion of axially chiral tetraalkoxyresorcin[4]arenes (cyclochiral resorcinarenes) into the related tetrakis(triflates) in high yields is described; this provides an efficient source of chiral materials for use in palladium-catalyzed transformations, including the reductive removal of triflate groups and the synthesis of compounds that are formally derived from 3-aminophenol, providing axially chiral derivatives that are nitrogen-substituted on the upper rim.

Original language	English
Pages (from-to)	3016-3025
Number of pages	10
Journal	European Journal of Organic Chemistry
Volume	2011
Issue number	16
DOIs	https://doi.org/10.1002/ejoc.201100122
Publication status	Published - 2011

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10.1002/ejoc.201100122

Cite this

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title = "C4-symmetric alkoxyresorcin[4]arene triflates: The use of palladium-catalyzed reactions in the synthesis of axially chiral derivatives with amino- and/or alkoxy-substituents",

abstract = "The conversion of axially chiral tetraalkoxyresorcin[4]arenes (cyclochiral resorcinarenes) into the related tetrakis(triflates) in high yields is described; this provides an efficient source of chiral materials for use in palladium-catalyzed transformations, including the reductive removal of triflate groups and the synthesis of compounds that are formally derived from 3-aminophenol, providing axially chiral derivatives that are nitrogen-substituted on the upper rim.",

author = "{Bulman Page}, {Philip C.} and Bygrave, {Terence R.} and Yohan Chan and Harry Heaney and Vickie McKee",

year = "2011",

doi = "10.1002/ejoc.201100122",

language = "English",

volume = "2011",

pages = "3016--3025",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley",

number = "16",

}

C4-symmetric alkoxyresorcin[4]arene triflates: The use of palladium-catalyzed reactions in the synthesis of axially chiral derivatives with amino- and/or alkoxy-substituents. / Bulman Page, Philip C.; Bygrave, Terence R.; Chan, Yohan et al.

In: European Journal of Organic Chemistry, Vol. 2011, No. 16, 2011, p. 3016-3025.

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

TY - JOUR

T1 - C4-symmetric alkoxyresorcin[4]arene triflates: The use of palladium-catalyzed reactions in the synthesis of axially chiral derivatives with amino- and/or alkoxy-substituents

AU - Bulman Page, Philip C.

AU - Bygrave, Terence R.

AU - Chan, Yohan

AU - Heaney, Harry

AU - McKee, Vickie

PY - 2011

Y1 - 2011

N2 - The conversion of axially chiral tetraalkoxyresorcin[4]arenes (cyclochiral resorcinarenes) into the related tetrakis(triflates) in high yields is described; this provides an efficient source of chiral materials for use in palladium-catalyzed transformations, including the reductive removal of triflate groups and the synthesis of compounds that are formally derived from 3-aminophenol, providing axially chiral derivatives that are nitrogen-substituted on the upper rim.

AB - The conversion of axially chiral tetraalkoxyresorcin[4]arenes (cyclochiral resorcinarenes) into the related tetrakis(triflates) in high yields is described; this provides an efficient source of chiral materials for use in palladium-catalyzed transformations, including the reductive removal of triflate groups and the synthesis of compounds that are formally derived from 3-aminophenol, providing axially chiral derivatives that are nitrogen-substituted on the upper rim.

U2 - 10.1002/ejoc.201100122

DO - 10.1002/ejoc.201100122

M3 - Article

VL - 2011

SP - 3016

EP - 3025

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 16

ER -