Tin(ii) chloride assisted synthesis of N-protected γ-amino β-keto esters through semipinacol rearrangement

Literature Information

Publication Date 2010-08-24
DOI 10.1039/C0OB00199F
Impact Factor 3.876
Authors

Anupam Bandyopadhyay, Neha Agrawal, Sachitanand M. Mali, Sandip V. Jadhav, Hosahudya N. Gopi


View Original

Abstract

A facile synthetic route for the preparation of N-protected γ-amino β-keto esters from amino aldehydes and ethyl diazoacetate is described. The two component coupling is facilitated by tin(II) chloride followed by semipinacol rearrangement leading to the product in quantitative yield. The reaction is mild, instantaneous and compatible with Boc-, Fmoc- and Cbz-amino protecting groups.

Related Literature

Polymer reinforced carbon fiber interfaces for high energy density structural lithium-ion batteries

Kathleen Moyer, Nora Ait Boucherbil, Murtaza Zohair, Janna Eaves-Rathert, Cary L. Pint

2020-03-31 Communication

DOI: 10.1039/D0SE00263A

Inside front cover

Cover

DOI: 10.1039/D0SE90041A

From non-innocent to guilty: on the role of redox-active ligands in the electro-assisted reduction of CO2 mediated by a cobalt(ii)-polypyridyl complex

N. Queyriaux, K. Abel, J. Fize, J. Pécaut, M. Orio, L. Hammarström

2020-05-13 Paper

DOI: 10.1039/D0SE00570C

An efficient bi-functional permselective separator coated with cubic type-Li7La3Zr2O12 and activated carbon for lithium–sulfur batteries

N. Angulakshmi, R. Baby Dhanalakshmi, Paulina Półrolniczak, Mariusz Walkowiak, Pengfei Xie, Xiaohui Tian, Yingke Zhou, A. Manuel Stephan

2020-05-06 Paper

DOI: 10.1039/D0SE00594K

Quantitative UPLC-MS/MS analysis of the gut microbial co-metabolites phenylacetylglutamine, 4-cresyl sulphate and hippurate in human urine: INTERMAP Study

Philip A. Clarke, Magda Bictash, Ian J. Brown, Mark Fidock, Thomas Ryckmans, Queenie Chan, Jeremiah Stamler

2011-10-19 Paper

DOI: 10.1039/C1AY05427A

Apparatus

Other

DOI: 10.1039/AN8992400194

A novel nonheme manganese(ii) complex for (electro) catalytic oxidation of water

Dattaprasad D. Narulkar, Anil Kumar U., Sunder N. Dhuri, Anil Kumar Vardhaman

2020-03-12 Communication

DOI: 10.1039/D0SE00232A

A fluorescence nanoprobe for detecting the effect of different oxygen and nutrient conditions on breast cancer cells’ migration and invasion

Ping Zhou, Bo Liu, Mingming Luan, Na Li, Bo Tang

2021-05-25 Communication

DOI: 10.1039/D1BM00619C

Metal-free 2D/2D heterostructured photocatalyst of black phosphorus/covalent triazine-based frameworks for water splitting and pollutant degradation

Yilin Chen, Lvting Wang, Mingyue Tan, Yingying Xiao, Bifen Gao, Bizhou Lin

2020-05-18 Paper

DOI: 10.1039/D0SE00394H

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.