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Easily Accessible and Highly Tunable Bisphosphine Ligands for Asymmetric Hydroformylation of Terminal and Internal Alkenes

An efficient methodology for synthesizing a small library of easily tunable and sterically bulky ligands for asymmetric hydroformylation (AHF) has been reported. Five groups of alkene substrates have been tested with excellent conversions, moderate‐to‐excellent regio‐ and enantioselectivities. Among... Full description

Journal Title: Chemistry – A European Journal 07 April 2014, Vol.20(15), pp.4357-4362
Main Author: Xu, Kun
Other Authors: Zheng, Xin , Wang, Zhiyong , Zhang, Xumu
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201304684
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recordid: wj10.1002/chem.201304684
title: Easily Accessible and Highly Tunable Bisphosphine Ligands for Asymmetric Hydroformylation of Terminal and Internal Alkenes
format: Article
creator:
  • Xu, Kun
  • Zheng, Xin
  • Wang, Zhiyong
  • Zhang, Xumu
subjects:
  • Alkenes
  • Enantioselectivity
  • Hydroformylation
  • Ligands
  • Synthetic Methods
ispartof: Chemistry – A European Journal, 07 April 2014, Vol.20(15), pp.4357-4362
description: An efficient methodology for synthesizing a small library of easily tunable and sterically bulky ligands for asymmetric hydroformylation (AHF) has been reported. Five groups of alkene substrates have been tested with excellent conversions, moderate‐to‐excellent regio‐ and enantioselectivities. Among the best result of the reported literature, application of ligand in the highly selective AHF of the challenging substrate 2,5‐dihydrofuran yielded almost one isomer in up to 99 % conversion along with enantiomeric excesses () of up to 92 %. Highly enantioselective AHF of dihydropyrrole substrates is achieved using the same ligand, with up to 95 %  and up to >1:50 β‐isomer/α‐isomer ratio. An efficient method for the easy and tunable synthesis of a series of asymmetric hydroformylation (AHF) ligands from low‐cost, commercially available starting materials has been reported. These ligands can give excellent conversions and moderate to excellent regio‐ and enantioselectivities for a broad range of mono‐ and disubstituted alkenes with a low catalyst loading (substrate‐to‐catalyst ratios (S/C) of 1000:1 to 3000:1).
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201304684
fulltext: fulltext
issn:
  • 0947-6539
  • 09476539
  • 1521-3765
  • 15213765
url: Link


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titleEasily Accessible and Highly Tunable Bisphosphine Ligands for Asymmetric Hydroformylation of Terminal and Internal Alkenes
creatorXu, Kun ; Zheng, Xin ; Wang, Zhiyong ; Zhang, Xumu
ispartofChemistry – A European Journal, 07 April 2014, Vol.20(15), pp.4357-4362
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subjectAlkenes ; Enantioselectivity ; Hydroformylation ; Ligands ; Synthetic Methods
descriptionAn efficient methodology for synthesizing a small library of easily tunable and sterically bulky ligands for asymmetric hydroformylation (AHF) has been reported. Five groups of alkene substrates have been tested with excellent conversions, moderate‐to‐excellent regio‐ and enantioselectivities. Among the best result of the reported literature, application of ligand in the highly selective AHF of the challenging substrate 2,5‐dihydrofuran yielded almost one isomer in up to 99 % conversion along with enantiomeric excesses () of up to 92 %. Highly enantioselective AHF of dihydropyrrole substrates is achieved using the same ligand, with up to 95 %  and up to >1:50 β‐isomer/α‐isomer ratio. An efficient method for the easy and tunable synthesis of a series of asymmetric hydroformylation (AHF) ligands from low‐cost, commercially available starting materials has been reported. These ligands can give excellent conversions and moderate to excellent regio‐ and enantioselectivities for a broad range of mono‐ and disubstituted alkenes with a low catalyst loading (substrate‐to‐catalyst ratios (S/C) of 1000:1 to 3000:1).
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titleEasily Accessible and Highly Tunable Bisphosphine Ligands for Asymmetric Hydroformylation of Terminal and Internal Alkenes
descriptionAn efficient methodology for synthesizing a small library of easily tunable and sterically bulky ligands for asymmetric hydroformylation (AHF) has been reported. Five groups of alkene substrates have been tested with excellent conversions, moderate‐to‐excellent regio‐ and enantioselectivities. Among the best result of the reported literature, application of ligand in the highly selective AHF of the challenging substrate 2,5‐dihydrofuran yielded almost one isomer in up to 99 % conversion along with enantiomeric excesses () of up to 92 %. Highly enantioselective AHF of dihydropyrrole substrates is achieved using the same ligand, with up to 95 %  and up to >1:50 β‐isomer/α‐isomer ratio. An efficient method for the easy and tunable synthesis of a series of asymmetric hydroformylation (AHF) ligands from low‐cost, commercially available starting materials has been reported. These ligands can give excellent conversions and moderate to excellent regio‐ and enantioselectivities for a broad range of mono‐ and disubstituted alkenes with a low catalyst loading (substrate‐to‐catalyst ratios (S/C) of 1000:1 to 3000:1).
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titleEasily Accessible and Highly Tunable Bisphosphine Ligands for Asymmetric Hydroformylation of Terminal and Internal Alkenes
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abstractAn efficient methodology for synthesizing a small library of easily tunable and sterically bulky ligands for asymmetric hydroformylation (AHF) has been reported. Five groups of alkene substrates have been tested with excellent conversions, moderate‐to‐excellent regio‐ and enantioselectivities. Among the best result of the reported literature, application of ligand in the highly selective AHF of the challenging substrate 2,5‐dihydrofuran yielded almost one isomer in up to 99 % conversion along with enantiomeric excesses () of up to 92 %. Highly enantioselective AHF of dihydropyrrole substrates is achieved using the same ligand, with up to 95 %  and up to >1:50 β‐isomer/α‐isomer ratio. An efficient method for the easy and tunable synthesis of a series of asymmetric hydroformylation (AHF) ligands from low‐cost, commercially available starting materials has been reported. These ligands can give excellent conversions and moderate to excellent regio‐ and enantioselectivities for a broad range of mono‐ and disubstituted alkenes with a low catalyst loading (substrate‐to‐catalyst ratios (S/C) of 1000:1 to 3000:1).
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pubWILEY‐VCH Verlag
doi10.1002/chem.201304684
pages4357-4362
date2014-04-07