Evaluation of the chiral DIANANE backbone as ligand for organolithium reagents

Jezabel Praz; Laure Guénée; Sarwar Aziz; Albrecht Berkessel; Alexandre Alexakis

doi:10.1002/adsc.201101016

Evaluation of the chiral DIANANE backbone as ligand for organolithium reagents

Jezabel Praz
, Laure Guénée
, Sarwar Aziz
, Albrecht Berkessel
, Alexandre Alexakis

University of Geneva
University of Cologne

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

14 Scopus citations

Abstract

Novel endo,endo-2,5-diaminonorbonane-derived tertiary C ₂- symmetrical diamines were synthesized via the one-pot reductive amination of enantiomerically pure norbornane-2,5-dione. These ligands were applied to various catalytic reactions such as asymmetric deprotonation, asymmetric bromine-lithium exchange, and enantioselective addition of aryl- and allkylithium reagents to aromatic aldimines.

Original language	English
Pages (from-to)	1780-1790
Number of pages	11
Journal	Advanced Synthesis and Catalysis
Volume	354
Issue number	9
DOIs	https://doi.org/10.1002/adsc.201101016
State	Published - 18 Jun 2012
Externally published	Yes

Keywords

asymmetric catalysis
bromine-lithium exchange
deprotonation
endo,endo-2,5-diaminonorbonane derivatives
nucleophilic addition
organolithium compounds

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10.1002/adsc.201101016

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title = "Evaluation of the chiral DIANANE backbone as ligand for organolithium reagents",

abstract = "Novel endo,endo-2,5-diaminonorbonane-derived tertiary C 2- symmetrical diamines were synthesized via the one-pot reductive amination of enantiomerically pure norbornane-2,5-dione. These ligands were applied to various catalytic reactions such as asymmetric deprotonation, asymmetric bromine-lithium exchange, and enantioselective addition of aryl- and allkylithium reagents to aromatic aldimines.",

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doi = "10.1002/adsc.201101016",

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AU - Praz, Jezabel

AU - Guénée, Laure

AU - Aziz, Sarwar

AU - Berkessel, Albrecht

AU - Alexakis, Alexandre

PY - 2012/6/18

Y1 - 2012/6/18

N2 - Novel endo,endo-2,5-diaminonorbonane-derived tertiary C 2- symmetrical diamines were synthesized via the one-pot reductive amination of enantiomerically pure norbornane-2,5-dione. These ligands were applied to various catalytic reactions such as asymmetric deprotonation, asymmetric bromine-lithium exchange, and enantioselective addition of aryl- and allkylithium reagents to aromatic aldimines.

AB - Novel endo,endo-2,5-diaminonorbonane-derived tertiary C 2- symmetrical diamines were synthesized via the one-pot reductive amination of enantiomerically pure norbornane-2,5-dione. These ligands were applied to various catalytic reactions such as asymmetric deprotonation, asymmetric bromine-lithium exchange, and enantioselective addition of aryl- and allkylithium reagents to aromatic aldimines.

KW - asymmetric catalysis

KW - bromine-lithium exchange

KW - deprotonation

KW - endo,endo-2,5-diaminonorbonane derivatives

KW - nucleophilic addition

KW - organolithium compounds

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DO - 10.1002/adsc.201101016

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SN - 1615-4150

VL - 354

SP - 1780

EP - 1790

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 9

ER -

Evaluation of the chiral DIANANE backbone as ligand for organolithium reagents

Abstract

Keywords

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