Asymmetric stepwise reductive amination of sulfonamides, sulfamates, and a phosphinamide by nickel catalysis

Asymmetric stepwise reductive amination of sulfonamides, sulfamates, and a phosphinamide by nickel catalysis

Asymmetric reductive amination of poorly nucleophilic sulfonamides was realized in the presence of nickel catalysts and titanium alkoxide. A wide range of ketones, including enolizable ketones and some biaryl ones, were converted into sulfonamides in excellent enantiomeric excess. The cyclization of...

Full description

Saved in:
Bibliographic Details
Main Authors: Zhao, Xiaohu, Xu, Haiyan, Huang, Xiaolei, Zhou, Steve Jianrong
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2021
Subjects:
Science::Chemistry
Chiral Alkylamines
Nickel Catalysis
Online Access:https://hdl.handle.net/10356/146874
Tags: Add Tag
No Tags, Be the first to tag this record!
Institution: Nanyang Technological University
Language: English
id sg-ntu-dr.10356-146874
record_format dspace
spelling sg-ntu-dr.10356-1468742021-03-12T05:15:14Z Asymmetric stepwise reductive amination of sulfonamides, sulfamates, and a phosphinamide by nickel catalysis Zhao, Xiaohu Xu, Haiyan Huang, Xiaolei Zhou, Steve Jianrong School of Physical and Mathematical Sciences Science::Chemistry Chiral Alkylamines Nickel Catalysis Asymmetric reductive amination of poorly nucleophilic sulfonamides was realized in the presence of nickel catalysts and titanium alkoxide. A wide range of ketones, including enolizable ketones and some biaryl ones, were converted into sulfonamides in excellent enantiomeric excess. The cyclization of sulfamates and intermolecular reductive amination of a diarylphosphinamide were also successful. Formic acid was used as a safe and economic surrogate of high-pressure hydrogen gas. Agency for Science, Technology and Research (A*STAR) Economic Development Board (EDB) We thank Singapore GSK-EDB Trust Fund (2017 GSK-EDBgreen and sustainable manufacturing award) and SingaporeA*STAR Science &Engineering Research Council (AMEIRG A1783c0010) for financial support. We thank BenAshley for some initial experiments.X.Z. and H.X. contrib-uted equally to the experiments. 2021-03-12T05:15:14Z 2021-03-12T05:15:14Z 2019 Journal Article Zhao, X., Xu, H., Huang, X. & Zhou, S. J. (2019). Asymmetric stepwise reductive amination of sulfonamides, sulfamates, and a phosphinamide by nickel catalysis. Angewandte Chemie, 58(1), 292-296. https://dx.doi.org/10.1002/anie.201809930 0044-8249 https://hdl.handle.net/10356/146874 10.1002/anie.201809930 30375715 2-s2.0-85057970170 1 58 292 296 en A1783c0010 Angewandte Chemie © 2019 Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim. All rights reserved.
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Chiral Alkylamines
Nickel Catalysis
spellingShingle Science::Chemistry
Chiral Alkylamines
Nickel Catalysis
Zhao, Xiaohu
Xu, Haiyan
Huang, Xiaolei
Zhou, Steve Jianrong
Asymmetric stepwise reductive amination of sulfonamides, sulfamates, and a phosphinamide by nickel catalysis
description Asymmetric reductive amination of poorly nucleophilic sulfonamides was realized in the presence of nickel catalysts and titanium alkoxide. A wide range of ketones, including enolizable ketones and some biaryl ones, were converted into sulfonamides in excellent enantiomeric excess. The cyclization of sulfamates and intermolecular reductive amination of a diarylphosphinamide were also successful. Formic acid was used as a safe and economic surrogate of high-pressure hydrogen gas.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Zhao, Xiaohu
Xu, Haiyan
Huang, Xiaolei
Zhou, Steve Jianrong
format Article
author Zhao, Xiaohu
Xu, Haiyan
Huang, Xiaolei
Zhou, Steve Jianrong
author_sort Zhao, Xiaohu
title Asymmetric stepwise reductive amination of sulfonamides, sulfamates, and a phosphinamide by nickel catalysis
title_short Asymmetric stepwise reductive amination of sulfonamides, sulfamates, and a phosphinamide by nickel catalysis
title_full Asymmetric stepwise reductive amination of sulfonamides, sulfamates, and a phosphinamide by nickel catalysis
title_fullStr Asymmetric stepwise reductive amination of sulfonamides, sulfamates, and a phosphinamide by nickel catalysis
title_full_unstemmed Asymmetric stepwise reductive amination of sulfonamides, sulfamates, and a phosphinamide by nickel catalysis
title_sort asymmetric stepwise reductive amination of sulfonamides, sulfamates, and a phosphinamide by nickel catalysis
publishDate 2021
url https://hdl.handle.net/10356/146874
_version_ 1695706236291383296

Similar Items