Enantioselective nucleophilic difluoromethylation of aromatic aldehydes with Me(3)SiCF(2)SO(2)Ph and PhSO(2)CF(2)H reagents catalyzed by chiral quaternary ammonium salts

BACKGROUND: Although the nucleophilic difluoromethylation of aldehydes, ketones, and imines has been realized with PhSO(2)CF(2)H and related reagents, there are still no reports on the enantioselective nucleophilic reactions. RESULTS: With a chiral quaternary ammonium salt as the catalyst and KOH as...

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Autores principales: Ni, Chuanfa, Wang, Fang, Hu, Jinbo
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2008
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2486490/
https://www.ncbi.nlm.nih.gov/pubmed/18941491
http://dx.doi.org/10.3762/bjoc.4.21
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author Ni, Chuanfa
Wang, Fang
Hu, Jinbo
author_facet Ni, Chuanfa
Wang, Fang
Hu, Jinbo
author_sort Ni, Chuanfa
collection PubMed
description BACKGROUND: Although the nucleophilic difluoromethylation of aldehydes, ketones, and imines has been realized with PhSO(2)CF(2)H and related reagents, there are still no reports on the enantioselective nucleophilic reactions. RESULTS: With a chiral quaternary ammonium salt as the catalyst and KOH as the base, we describe the first enantioselective difluoromethylation of aromatic aldehydes with PhSO(2)CF(2)H or Me(3)SiCF(2)SO(2)Ph. The enantioselectivity is substrate-dependent and for 2-chlorinated benzaldehyde an ee up to 64% was obtained. CONCLUSION: These results provide some insights into the enantioselective nucleophilic difluoromethylation chemistry, which will stimulate further progress in this field.
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spelling pubmed-24864902008-10-20 Enantioselective nucleophilic difluoromethylation of aromatic aldehydes with Me(3)SiCF(2)SO(2)Ph and PhSO(2)CF(2)H reagents catalyzed by chiral quaternary ammonium salts Ni, Chuanfa Wang, Fang Hu, Jinbo Beilstein J Org Chem Full Research Paper BACKGROUND: Although the nucleophilic difluoromethylation of aldehydes, ketones, and imines has been realized with PhSO(2)CF(2)H and related reagents, there are still no reports on the enantioselective nucleophilic reactions. RESULTS: With a chiral quaternary ammonium salt as the catalyst and KOH as the base, we describe the first enantioselective difluoromethylation of aromatic aldehydes with PhSO(2)CF(2)H or Me(3)SiCF(2)SO(2)Ph. The enantioselectivity is substrate-dependent and for 2-chlorinated benzaldehyde an ee up to 64% was obtained. CONCLUSION: These results provide some insights into the enantioselective nucleophilic difluoromethylation chemistry, which will stimulate further progress in this field. Beilstein-Institut 2008-06-26 /pmc/articles/PMC2486490/ /pubmed/18941491 http://dx.doi.org/10.3762/bjoc.4.21 Text en Copyright © 2008, Ni et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Ni, Chuanfa
Wang, Fang
Hu, Jinbo
Enantioselective nucleophilic difluoromethylation of aromatic aldehydes with Me(3)SiCF(2)SO(2)Ph and PhSO(2)CF(2)H reagents catalyzed by chiral quaternary ammonium salts
title Enantioselective nucleophilic difluoromethylation of aromatic aldehydes with Me(3)SiCF(2)SO(2)Ph and PhSO(2)CF(2)H reagents catalyzed by chiral quaternary ammonium salts
title_full Enantioselective nucleophilic difluoromethylation of aromatic aldehydes with Me(3)SiCF(2)SO(2)Ph and PhSO(2)CF(2)H reagents catalyzed by chiral quaternary ammonium salts
title_fullStr Enantioselective nucleophilic difluoromethylation of aromatic aldehydes with Me(3)SiCF(2)SO(2)Ph and PhSO(2)CF(2)H reagents catalyzed by chiral quaternary ammonium salts
title_full_unstemmed Enantioselective nucleophilic difluoromethylation of aromatic aldehydes with Me(3)SiCF(2)SO(2)Ph and PhSO(2)CF(2)H reagents catalyzed by chiral quaternary ammonium salts
title_short Enantioselective nucleophilic difluoromethylation of aromatic aldehydes with Me(3)SiCF(2)SO(2)Ph and PhSO(2)CF(2)H reagents catalyzed by chiral quaternary ammonium salts
title_sort enantioselective nucleophilic difluoromethylation of aromatic aldehydes with me(3)sicf(2)so(2)ph and phso(2)cf(2)h reagents catalyzed by chiral quaternary ammonium salts
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2486490/
https://www.ncbi.nlm.nih.gov/pubmed/18941491
http://dx.doi.org/10.3762/bjoc.4.21
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AT wangfang enantioselectivenucleophilicdifluoromethylationofaromaticaldehydeswithme3sicf2so2phandphso2cf2hreagentscatalyzedbychiralquaternaryammoniumsalts
AT hujinbo enantioselectivenucleophilicdifluoromethylationofaromaticaldehydeswithme3sicf2so2phandphso2cf2hreagentscatalyzedbychiralquaternaryammoniumsalts

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