Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism

Palladium catalyzed allylic substitution reactions typically proceed via an outer sphere mechanism, yielding predominately linear products. Here, the authors report an inner sphere process for the allylic substitution of ketone enolates, giving branched products with up to three contiguous stereocen...

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Main Authors: Da-Chang Bai, Fei-Le Yu, Wan-Ying Wang, Di Chen, Hao Li, Qing-Rong Liu, Chang-Hua Ding, Bo Chen, Xue-Long Hou
Format: Article
Language:English
Published: Nature Portfolio 2016-06-01
Series:Nature Communications
Online Access:https://doi.org/10.1038/ncomms11806
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author Da-Chang Bai
Fei-Le Yu
Wan-Ying Wang
Di Chen
Hao Li
Qing-Rong Liu
Chang-Hua Ding
Bo Chen
Xue-Long Hou
author_facet Da-Chang Bai
Fei-Le Yu
Wan-Ying Wang
Di Chen
Hao Li
Qing-Rong Liu
Chang-Hua Ding
Bo Chen
Xue-Long Hou
author_sort Da-Chang Bai
collection DOAJ
description Palladium catalyzed allylic substitution reactions typically proceed via an outer sphere mechanism, yielding predominately linear products. Here, the authors report an inner sphere process for the allylic substitution of ketone enolates, giving branched products with up to three contiguous stereocentres.
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spelling doaj.art-a2190ea2df8449c6b683e64e74797d1d2022-12-21T18:03:58ZengNature PortfolioNature Communications2041-17232016-06-017111110.1038/ncomms11806Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanismDa-Chang Bai0Fei-Le Yu1Wan-Ying Wang2Di Chen3Hao Li4Qing-Rong Liu5Chang-Hua Ding6Bo Chen7Xue-Long Hou8State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of SciencesState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of SciencesState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of SciencesState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of SciencesState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of SciencesState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of SciencesState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of SciencesDepartment of Chemistry and Chemical Biology, Baker Laboratory, Cornell UniversityState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of SciencesPalladium catalyzed allylic substitution reactions typically proceed via an outer sphere mechanism, yielding predominately linear products. Here, the authors report an inner sphere process for the allylic substitution of ketone enolates, giving branched products with up to three contiguous stereocentres.https://doi.org/10.1038/ncomms11806
spellingShingle Da-Chang Bai
Fei-Le Yu
Wan-Ying Wang
Di Chen
Hao Li
Qing-Rong Liu
Chang-Hua Ding
Bo Chen
Xue-Long Hou
Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism
Nature Communications
title Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism
title_full Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism
title_fullStr Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism
title_full_unstemmed Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism
title_short Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism
title_sort palladium n heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner sphere mechanism
url https://doi.org/10.1038/ncomms11806
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