Chromium(II)-catalyzed enantioselective arylation of ketones

The chromium-catalyzed enantioselective addition of carbo halides to carbonyl compounds is an important transformation in organic synthesis. However, the corresponding catalytic enantioselective arylation of ketones has not been reported to date. Herein, we report the first Cr-catalyzed enantioselec...

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Main Authors: Gang Wang, Shutao Sun, Ying Mao, Zhiyu Xie, Lei Liu
Format: Article
Language:English
Published: Beilstein-Institut 2016-12-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.12.275
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author Gang Wang
Shutao Sun
Ying Mao
Zhiyu Xie
Lei Liu
author_facet Gang Wang
Shutao Sun
Ying Mao
Zhiyu Xie
Lei Liu
author_sort Gang Wang
collection DOAJ
description The chromium-catalyzed enantioselective addition of carbo halides to carbonyl compounds is an important transformation in organic synthesis. However, the corresponding catalytic enantioselective arylation of ketones has not been reported to date. Herein, we report the first Cr-catalyzed enantioselective addition of aryl halides to both arylaliphatic and aliphatic ketones with high enantioselectivity in an intramolecular version, providing facile access to enantiopure tetrahydronaphthalen-1-ols and 2,3-dihydro-1H-inden-1-ols containing a tertiary alcohol.
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spelling doaj.art-e2ca59882450497186868c1a2640fd172022-12-21T22:11:45ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-12-011212771277510.3762/bjoc.12.2751860-5397-12-275Chromium(II)-catalyzed enantioselective arylation of ketonesGang Wang0Shutao Sun1Ying Mao2Zhiyu Xie3Lei Liu4Shenzhen Research Institute of Shandong University, Shenzhen 518057, ChinaSchool of Pharmaceutical Sciences, Shandong University, Jinan 250012, ChinaSchool of Pharmaceutical Sciences, Shandong University, Jinan 250012, ChinaSchool of Pharmaceutical Sciences, Shandong University, Jinan 250012, ChinaShenzhen Research Institute of Shandong University, Shenzhen 518057, ChinaThe chromium-catalyzed enantioselective addition of carbo halides to carbonyl compounds is an important transformation in organic synthesis. However, the corresponding catalytic enantioselective arylation of ketones has not been reported to date. Herein, we report the first Cr-catalyzed enantioselective addition of aryl halides to both arylaliphatic and aliphatic ketones with high enantioselectivity in an intramolecular version, providing facile access to enantiopure tetrahydronaphthalen-1-ols and 2,3-dihydro-1H-inden-1-ols containing a tertiary alcohol.https://doi.org/10.3762/bjoc.12.275arylationasymmetric catalysischromiumketonetertiary alcohol
spellingShingle Gang Wang
Shutao Sun
Ying Mao
Zhiyu Xie
Lei Liu
Chromium(II)-catalyzed enantioselective arylation of ketones
Beilstein Journal of Organic Chemistry
arylation
asymmetric catalysis
chromium
ketone
tertiary alcohol
title Chromium(II)-catalyzed enantioselective arylation of ketones
title_full Chromium(II)-catalyzed enantioselective arylation of ketones
title_fullStr Chromium(II)-catalyzed enantioselective arylation of ketones
title_full_unstemmed Chromium(II)-catalyzed enantioselective arylation of ketones
title_short Chromium(II)-catalyzed enantioselective arylation of ketones
title_sort chromium ii catalyzed enantioselective arylation of ketones
topic arylation
asymmetric catalysis
chromium
ketone
tertiary alcohol
url https://doi.org/10.3762/bjoc.12.275
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AT shutaosun chromiumiicatalyzedenantioselectivearylationofketones
AT yingmao chromiumiicatalyzedenantioselectivearylationofketones
AT zhiyuxie chromiumiicatalyzedenantioselectivearylationofketones
AT leiliu chromiumiicatalyzedenantioselectivearylationofketones