Carbene-catalyzed α-carbon amination of chloroaldehydes for enantioselective access to dihydroquinoxaline derivatives

Carbene-catalyzed α-carbon amination of chloroaldehydes for enantioselective access to dihydroquinoxaline derivatives

An NHC-catalyzed α-carbon amination of chloroaldehydes was developed. Cyclohexadiene-1,2-diimines are used as amination reagents and four-atom synthons. Our reaction affords optically enriched dihydroquinoxalines that are core structures in natural products and synthetic bioactive molecules.

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Main Authors: Huang, Ruoyan, Chen, Xingkuan, Mou, Chengli, Luo, Guoyong, Li, Yongjia, Li, Xiangyang, Xue, Wei, Jin, Zhichao, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry::Organic chemistry
Enantioselectivity
N-Heterocyclic Carbene Catalysis
Online Access:https://hdl.handle.net/10356/137763
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1377632023-02-28T19:46:08Z Carbene-catalyzed α-carbon amination of chloroaldehydes for enantioselective access to dihydroquinoxaline derivatives Huang, Ruoyan Chen, Xingkuan Mou, Chengli Luo, Guoyong Li, Yongjia Li, Xiangyang Xue, Wei Jin, Zhichao Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry::Organic chemistry Enantioselectivity N-Heterocyclic Carbene Catalysis An NHC-catalyzed α-carbon amination of chloroaldehydes was developed. Cyclohexadiene-1,2-diimines are used as amination reagents and four-atom synthons. Our reaction affords optically enriched dihydroquinoxalines that are core structures in natural products and synthetic bioactive molecules. NRF (Natl Research Foundation, S’pore) ASTAR (Agency for Sci., Tech. and Research, S’pore) MOE (Min. of Education, S’pore) Accepted version 2020-04-14T02:49:36Z 2020-04-14T02:49:36Z 2019 Journal Article Huang, R., Chen, X., Mou, C., Luo, G., Li, Y., Li, X., … Chi, R. Y. (2019). Carbene-catalyzed α-carbon amination of chloroaldehydes for enantioselective access to dihydroquinoxaline derivatives. Organic Letters, 21(11), 4340-4344. doi:10.1021/acs.orglett.9b01520 1523-7060 https://hdl.handle.net/10356/137763 10.1021/acs.orglett.9b01520 31117715 2-s2.0-85066927070 11 21 4340 4344 en Organic Letters This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.9b01520 application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry::Organic chemistry
Enantioselectivity
N-Heterocyclic Carbene Catalysis
spellingShingle Science::Chemistry::Organic chemistry
Enantioselectivity
N-Heterocyclic Carbene Catalysis
Huang, Ruoyan
Chen, Xingkuan
Mou, Chengli
Luo, Guoyong
Li, Yongjia
Li, Xiangyang
Xue, Wei
Jin, Zhichao
Chi, Robin Yonggui
Carbene-catalyzed α-carbon amination of chloroaldehydes for enantioselective access to dihydroquinoxaline derivatives
description An NHC-catalyzed α-carbon amination of chloroaldehydes was developed. Cyclohexadiene-1,2-diimines are used as amination reagents and four-atom synthons. Our reaction affords optically enriched dihydroquinoxalines that are core structures in natural products and synthetic bioactive molecules.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Huang, Ruoyan
Chen, Xingkuan
Mou, Chengli
Luo, Guoyong
Li, Yongjia
Li, Xiangyang
Xue, Wei
Jin, Zhichao
Chi, Robin Yonggui
format Article
author Huang, Ruoyan
Chen, Xingkuan
Mou, Chengli
Luo, Guoyong
Li, Yongjia
Li, Xiangyang
Xue, Wei
Jin, Zhichao
Chi, Robin Yonggui
author_sort Huang, Ruoyan
title Carbene-catalyzed α-carbon amination of chloroaldehydes for enantioselective access to dihydroquinoxaline derivatives
title_short Carbene-catalyzed α-carbon amination of chloroaldehydes for enantioselective access to dihydroquinoxaline derivatives
title_full Carbene-catalyzed α-carbon amination of chloroaldehydes for enantioselective access to dihydroquinoxaline derivatives
title_fullStr Carbene-catalyzed α-carbon amination of chloroaldehydes for enantioselective access to dihydroquinoxaline derivatives
title_full_unstemmed Carbene-catalyzed α-carbon amination of chloroaldehydes for enantioselective access to dihydroquinoxaline derivatives
title_sort carbene-catalyzed α-carbon amination of chloroaldehydes for enantioselective access to dihydroquinoxaline derivatives
publishDate 2020
url https://hdl.handle.net/10356/137763
_version_ 1759857445278056448

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