Mixed carboxylic–sulfonic anhydride in reaction with imines: a straightforward route to water-soluble β-lactams via a Staudinger-type reaction

Literature Information

Publication Date 2018-05-08
DOI 10.1039/C8OB00768C
Impact Factor 3.876
Authors

Olga Bakulina, Dmitry Dar'in, Mikhail Krasavin


View Original

Abstract

The first example of employing a mixed carboxylic–sulfonic anhydride in reaction with imines is reported. Unlike its well-studied isostere homophthalic anhydride, benzo[c][1,2]oxathiin-3(4H)-one 1,1-dioxide gave no product of a formal [4 + 2] cycloaddition and only followed an alternative reaction pathway toward β-lactams, presumably, via a formal [2 + 2] cycloaddition (a Staudinger-type reaction). Optimized reaction conditions involve the use of triethylamine as a base promoter, which also allows isolating the product β-lactam benzene sulfonic acids as respective triethylammonium salts by conventional column chromatography. The reaction shows some preference to trans-isomer formation; pure diastereomers can be isolated in some cases.

Related Literature

Back cover

Cover

DOI: 10.1039/D0QO90038A

The protecting group enabled para-selective C–H benzylation of anilides via iron(ii) catalysis: a convenient approach for the synthesis of triarylmethanes

Yi Han, Guobao Li, Lingling Liu, Chenyang Dai, Da-Qing Shi, Yingsheng Zhao

2020-06-10 Research Article

DOI: 10.1039/D0QO00402B

Straight access to highly fluorescent angular indolocarbazoles via merging Au- and Mo-catalysis

Fernando Martínez-Lara, Anisley Suárez, Samuel Suárez-Pantiga, M. José Tapia, Roberto Sanz

2020-06-10 Research Article

DOI: 10.1039/D0QO00405G

Synthesis of a non-natural glucose-2-phosphate ester able to dupe the acc system of Agrobacterium fabrum

Si-Zhe Li, Armelle Vigouroux, Mohammed Ahmar, Abbas El Sahili, Laurent Soulère, Laïla Sago, David Cornu, Solange Moréra, Yves Queneau

2019-01-04 Paper

DOI: 10.1039/C8OB03086C

Facile synthesis of the daphnane and tigliane framework by semi-flow tube-based-bubbling photooxidation and diastereoselective conjugate addition

Zhengwei Ding, Zhi Liu, Guanghu Tong, Linlin Hu, Yangqing He, Yueyun Bao, Zhouhang Lei, Hailong Zhang

2020-06-09 Research Article

DOI: 10.1039/D0QO00424C

A semipinacol rearrangement of vinylogous α-ketol cocatalyzed by a cinchona-based primary amine and N-Boc-phenylglycines: mechanisms, roles of catalysts and the origin of enantioselectivity

Chao-Xian Yan, Fang-Ling Yang, Ka Lu, Xing Yang, Pan-Pan Zhou, Xiangfeng Shao

2020-06-05 Research Article

DOI: 10.1039/D0QO00506A

Oxidative N-heterocyclic carbene-catalyzed [3 + 3] annulation reaction of enals with benzofuran-3-ones: efficient access to benzofuran-fused δ-lactones

Zhan-Yong Wang, Ting Yang, Kai-Kai Wang, Rongxiang Chen, Menghan Liu

2020-03-17 Research Article

DOI: 10.1039/D0QO00161A

Direct organocatalytic asymmetric Michael reaction of fluorine hemiaminal-type nucleophile to 4-nitro-5-styrylisoxazoles

Luyao Li, Bo Zhu, Huihui Fan, Zhiyong Jiang, Junbiao Chang

2020-04-17 Research Article

DOI: 10.1039/D0QO00348D

Hydroaminoalkylation of sterically hindered alkenes with N,N-dimethyl anilines using a scandium catalyst

Jianhong Su, Yiqun Zhou, Xin Xu

2018-12-10 Paper

DOI: 10.1039/C8OB02657B

Biosynthesis of bioactive natural products from Basidiomycota

Yit-Heng Chooi

2018-12-14 Review Article

DOI: 10.1039/C8OB02774A

You might also like

Compound Q&A

What industries use (1R,3S)-1,3-Cyclopentanediol (CAS: 16326-97-9)?

(1R,3S)-1,3-Cyclopentanediol finds applications in various industries. In the ph...

16326-97-9(1R,3S)-1,3-Cyclopen...
Compound Q&A

What precautions should be taken when handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine (CAS: 637-31-0)?

When handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine, it i...

637-31-0N'-[4-(Dimethylamino...
Compound Q&A

Are there alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine (CAS: 1352318-16-1) in synthesis?

There are several alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine in ...

1352318-16-15-(2,4-Difluoropheny...
Compound Q&A

What regulatory guidelines apply to 1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6)?

1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6) must comply with the Globally...

382141-68-61-(3-Methoxyphenoxy)...
Compound Q&A

Is Tetrodotoxin Citrate (CAS: 18660-81-6) safe?

Tetrodotoxin Citrate is extremely dangerous and should be handled with extreme c...

18660-81-6Tetrodotoxin Citrate
Compound Q&A

What are the main uses of 2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9)?

2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9) i...

225641-84-92-Methyl-2-propanyl ...
Compound Q&A

How should waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) be handled?

Waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) ...

16261-80-64-(2-Hydroxyhexafluo...
Compound Q&A

How is 2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl}carbamate (CAS: 102507-19-7) typically synthesized?

2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl...

102507-19-72-Methyl-2-propanyl ...
Compound Q&A

What is Benzeneethanamine, α-ethyl-, hydrochloride (1:1) (CAS: 20735-15-3)?

Benzeneethanamine, α-ethyl-, hydrochloride (1:1) is an organic compound with the...

20735-15-3Benzeneethanamine, α...
Compound Q&A

Are there alternatives to 3-{(E)-[4-(Dimethylamino)phenyl]diazenyl}benzoic acid (CAS: 20691-84-3) in synthesis?

In the synthesis of compounds similar to 3-{(E)-[4-(Dimethylamino)phenyl]diazeny...

20691-84-33-{(E)-[4-(Dimethyla...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.