Twisted amide analogues of Tröger's base

Josep Artacho; Erhad Ascic; Toni Rantanen; Josefine Karlsson; Carl Johan Wallentin; Ruiyao Wang; Ola F. Wendt; Michael Harmata; Victor Snieckus; Kenneth Wärnmark

doi:10.1002/chem.201103228

Twisted amide analogues of Tröger's base

Josep Artacho
, Erhad Ascic
, Toni Rantanen
, Josefine Karlsson
, Carl Johan Wallentin
, Ruiyao Wang
, Ola F. Wendt
, Michael Harmata
, Victor Snieckus
, Kenneth Wärnmark^*

^*Corresponding author for this work

Lund University
Queen's University Kingston
University of Missouri

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

34 Citations (Scopus)

Abstract

Let's do the twist: The first twisted bis-amide (see figure) is obtained by the benzylic oxidation of Tröger's base (TB). Kinetic studies of its acidic hydrolysis reveal that the hydrolysis is to a large extent funneled through doubly protonated species.

Original language	English
Pages (from-to)	1038-1042
Number of pages	5
Journal	Chemistry - A European Journal
Volume	18
Issue number	4
DOIs	https://doi.org/10.1002/chem.201103228
Publication status	Published - 23 Jan 2012
Externally published	Yes

Keywords

Tröger's base
X-ray structures
hydrolysis
oxidation
twisted amides

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10.1002/chem.201103228

Cite this

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title = "Twisted amide analogues of Tr{\"o}ger's base",

abstract = "Let's do the twist: The first twisted bis-amide (see figure) is obtained by the benzylic oxidation of Tr{\"o}ger's base (TB). Kinetic studies of its acidic hydrolysis reveal that the hydrolysis is to a large extent funneled through doubly protonated species.",

keywords = "Tr{\"o}ger's base, X-ray structures, hydrolysis, oxidation, twisted amides",

author = "Josep Artacho and Erhad Ascic and Toni Rantanen and Josefine Karlsson and Wallentin, \{Carl Johan\} and Ruiyao Wang and Wendt, \{Ola F.\} and Michael Harmata and Victor Snieckus and Kenneth W{\"a}rnmark",

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language = "English",

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AU - Artacho, Josep

AU - Ascic, Erhad

AU - Rantanen, Toni

AU - Karlsson, Josefine

AU - Wallentin, Carl Johan

AU - Wang, Ruiyao

AU - Wendt, Ola F.

AU - Harmata, Michael

AU - Snieckus, Victor

AU - Wärnmark, Kenneth

PY - 2012/1/23

Y1 - 2012/1/23

N2 - Let's do the twist: The first twisted bis-amide (see figure) is obtained by the benzylic oxidation of Tröger's base (TB). Kinetic studies of its acidic hydrolysis reveal that the hydrolysis is to a large extent funneled through doubly protonated species.

AB - Let's do the twist: The first twisted bis-amide (see figure) is obtained by the benzylic oxidation of Tröger's base (TB). Kinetic studies of its acidic hydrolysis reveal that the hydrolysis is to a large extent funneled through doubly protonated species.

KW - Tröger's base

KW - X-ray structures

KW - hydrolysis

KW - oxidation

KW - twisted amides

UR - https://www.scopus.com/pages/publications/84862944288

U2 - 10.1002/chem.201103228

DO - 10.1002/chem.201103228

M3 - Article

AN - SCOPUS:84862944288

SN - 0947-6539

VL - 18

SP - 1038

EP - 1042

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 4

ER -

Twisted amide analogues of Tröger's base

Abstract

Keywords

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