A new chiral phenomenon of orientational chirality, its synthetic control and computational study.

and sonogashira coupling atropisomerism orientational chirality rotamer suzuki-miyaura coupling

Journal

Frontiers in chemistry
ISSN: 2296-2646
Titre abrégé: Front Chem
Pays: Switzerland
ID NLM: 101627988

Informations de publication

Date de publication:
2022
Historique:
received: 28 11 2022
accepted: 19 12 2022
entrez: 23 1 2023
pubmed: 24 1 2023
medline: 24 1 2023
Statut: epublish

Résumé

A new type of chirality, orientational chirality, consisting of a tetrahedron center and a remotely anchored blocker, has been discovered. The key structural element of this chirality is characterized by multiple orientations directed by a through-space functional group. The multi-step synthesis of orientational chiral targets was conducted by taking advantage of asymmetric nucleophilic addition, Suzuki-Miyaura cross-coupling and Sonogashira coupling. An unprecedented catalytic species showing a five-membered ring consisting of C (sp

Identifiants

pubmed: 36688043
doi: 10.3389/fchem.2022.1110240
pii: 1110240
pmc: PMC9850238
doi:

Types de publication

Journal Article

Langues

eng

Pagination

1110240

Informations de copyright

Copyright © 2023 Jin, Xu, Tang, Wang, Wang, Pan, Zhang, Yuan, Rahman, Aquino, Lischka and Li.

Déclaration de conflit d'intérêts

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Références

Natl Sci Rev. 2020 Apr 02;8(1):nwaa205
pubmed: 34691558
Angew Chem Int Ed Engl. 2018 Mar 26;57(14):3661-3665
pubmed: 29388296
J Org Chem. 2022 May 6;87(9):5976-5986
pubmed: 35442684
Nat Commun. 2020 Nov 23;11(1):5935
pubmed: 33230219
Acc Chem Res. 2020 Jul 21;53(7):1279-1292
pubmed: 32649172
J Am Chem Soc. 2007 Oct 31;129(43):12948-9
pubmed: 17918850
Research (Wash D C). 2019 Jun 27;2019:6717104
pubmed: 31549078
Chem Rev. 2012 Mar 14;112(3):1463-535
pubmed: 22017405
J Am Chem Soc. 2022 Jan 19;144(2):1056-1065
pubmed: 34990550
Acc Chem Res. 2003 Sep;36(9):659-67
pubmed: 12974649
Science. 2011 Jul 15;333(6040):339-41
pubmed: 21764746
Research (Wash D C). 2020 Apr 22;2020:3839160
pubmed: 32395717
Biopolymers. 1997;43(3):219-66
pubmed: 9277134
Chem Soc Rev. 2017 Dec 7;46(23):7399-7420
pubmed: 29051927
J Med Chem. 1995 Feb 17;38(4):585-6
pubmed: 7861405
Front Chem. 2022 Mar 31;10:860398
pubmed: 35433628
Angew Chem Int Ed Engl. 2001 Nov 19;40(22):4167-4173
pubmed: 29712120
Biophys J. 1998 Jul;75(1):422-7
pubmed: 9649402
Acc Chem Res. 2020 Mar 17;53(3):690-702
pubmed: 32142245
J Chem Phys. 2010 Apr 21;132(15):154104
pubmed: 20423165
Acc Chem Res. 2020 Feb 18;53(2):425-446
pubmed: 31820922
Angew Chem Int Ed Engl. 2021 Sep 20;60(39):21486-21493
pubmed: 34235834
Chemistry. 2022 Feb 1;28(7):e202104102
pubmed: 34962686
Angew Chem Int Ed Engl. 2020 Oct 19;59(43):18985-18989
pubmed: 32662085
ACS Appl Mater Interfaces. 2021 Dec 1;13(47):56413-56419
pubmed: 34784463
Cold Spring Harb Symp Quant Biol. 1983;47 Pt 1:33-44
pubmed: 6574849
Chem Asian J. 2016 Feb 4;11(3):330-41
pubmed: 26395547
Research (Wash D C). 2022 Feb 16;2022:9847949
pubmed: 35265849
J Am Chem Soc. 2020 Sep 16;142(37):15686-15696
pubmed: 32845127
J Am Chem Soc. 2021 Jun 16;143(23):8772-8779
pubmed: 34085826
Natl Sci Rev. 2020 Mar;7(3):588-599
pubmed: 34692078
J Am Chem Soc. 2021 Jul 7;143(26):9991-10004
pubmed: 34161077
Chemistry. 2021 May 26;27(30):8013-8020
pubmed: 33830589
Research (Wash D C). 2020 Aug 4;2020:5689246
pubmed: 32832906
J Am Chem Soc. 2011 Mar 16;133(10):3304-7
pubmed: 21332140
Research (Wash D C). 2022 Aug 11;2022:9865108
pubmed: 36061818
J Am Chem Soc. 2021 Jan 13;143(1):114-120
pubmed: 33356232
Acc Chem Res. 2018 Feb 20;51(2):534-547
pubmed: 29419282
Research (Wash D C). 2020 Feb 28;2020:7873581
pubmed: 32190834
RSC Adv. 2019 Apr 16;9(21):11978-11985
pubmed: 35517000

Auteurs

Shengzhou Jin (S)

School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.

Ting Xu (T)

School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.

Yao Tang (Y)

Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX, United States.

Jia-Yin Wang (JY)

Continuous Flow Engineering Laboratory of National Petroleum and Chemical Industry, Changzhou University, Changzhou, Jiangsu, China.

Yu Wang (Y)

School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.

Junyi Pan (J)

School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.

Sai Zhang (S)

Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX, United States.

Qingkai Yuan (Q)

Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX, United States.

Anis Ur Rahman (AU)

Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX, United States.

Adelia J A Aquino (AJA)

4 Department of Mechanical Engineering, Texas Tech University, Lubbock, TX, United States.

Hans Lischka (H)

Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX, United States.

Guigen Li (G)

School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX, United States.

Classifications MeSH