Stereoselective Michael additions on α-aminoacrylates as the key step to an l-Oic analogue bearing a quaternary stereocenter

Literature Information

Publication Date 2019-12-16
DOI 10.1039/C9OB02084E
Impact Factor 3.876
Authors

Federico Maria Cecchinelli, Giuseppe Celentano, Alessandra Puglisi, Nicoletta Gaggero


View Original

Abstract

A novel, highly stereoselective route for pharmaceutically relevant octahydroindole-2-carboxylates bearing a quaternary stereocenter has been developed. The key chiral intermediates 3 have been prepared in good yields and enantiomeric excesses up to 98%. A broad substrate range has been tolerated under the reaction conditions.

Related Literature

Tumor microenvironment-responsive degradable silica nanoparticles: design principles and precision theranostic applications

Kaiyuan Tang, Zilu Liu, Zhijing Zhang, Shufan Duan, Hui Wang, Hui Yang, Dongliang Yang, Wenpei Fan

2023-11-29 Review Article

DOI: 10.1039/D3NH00388D

Inside back cover

2023-11-21 Cover

DOI: 10.1039/D3TA90252H

Solar light selective-harvesting eco-friendly colloidal quantum dots for transparent luminescent solar concentrators

Ehsan Hamzehpoor, Jiabin Liu, Xin Liu, Gurpreet Singh Selopal, Dmytro F. Perepichka, Zhiming M. Wang

2023-10-13 Paper

DOI: 10.1039/D3TA05351B

Albumin protein encapsulation into a ZIF-8 framework with Co-LDH-based hierarchical architectures for robust catalytic reduction

Maryam Chafiq, Abdelkarim Chaouiki, Tri Suhartono, Young Gun Ko

2023-10-30 Paper

DOI: 10.1039/D3TA03623E

Ultrahigh-quality graphene resonators by liquid-based strain-engineering

Mario Hofmann, Chi-Te Liang, Ya-Ping Hsieh

2023-11-02 Communication

DOI: 10.1039/D3NH00420A

Simple phenylpropanoids: recent advances in biological activities, biosynthetic pathways, and microbial production

Zhanpin Zhu, Ruibing Chen

2023-10-09 Review Article

DOI: 10.1039/D3NP00012E

Enabling isotropic Li growth via Li foil facet-engineering for high-performance Li metal batteries

Yanyan Liu, Shuyue Wang, Minghao Sun, Min Ling, Shaodong Zhou, Chengdu Liang

2023-10-02 Paper

DOI: 10.1039/D3TA05203F

You might also like

Compound Q&A

What regulatory guidelines apply to 6-Bromo-2-methylimidazo[1,2-a]pyrimidine (CAS: 1111638-05-1)?

6-Bromo-2-methylimidazo[1,2-a]pyrimidine (CAS: 1111638-05-1) falls under various...

1111638-05-16-Bromo-2-methylimid...
Compound Q&A

Are there alternatives to 1-Pyrrolidineethanol, β-methyl-α-phenyl-, (αS,βR) (CAS: 123620-80-4) in synthesis?

While there are no direct alternatives, similar compounds like 1-Pyrrolidineetha...

123620-80-41-Pyrrolidineethanol...
Compound Q&A

Is 4-Methyl-2,6-bis(2-methyl-2-propanyl)phenyl methylcarbamate (CAS: 1918-11-2) safe?

4-Methyl-2,6-bis(2-methyl-2-propanyl)phenyl methylcarbamate (CAS: 1918-11-2) is ...

1918-11-24-Methyl-2,6-bis(2-m...
Compound Q&A

How should 2-(3-Bromo-4-fluorophenyl)-1,3-dioxolane (CAS: 77771-04-1) be stored?

2-(3-Bromo-4-fluorophenyl)-1,3-dioxolane (CAS: 77771-04-1) should be stored in a...

77771-04-12-(3-Bromo-4-fluorop...
Compound Q&A

What are the physical and chemical properties of 4,5,6,7-Tetrahydro-1H-indazole hydrochloride (CAS: 18161-11-0)?

4,5,6,7-Tetrahydro-1H-indazole hydrochloride is a white crystalline solid with a...

18161-11-04,5,6,7-Tetrahydro-1...
Compound Q&A

What is (2R)-1-Methoxy-3-phenyl-2-propanamine (CAS: 59919-07-2)?

(2R)-1-Methoxy-3-phenyl-2-propanamine is a chiral organic compound with the CAS ...

59919-07-2(2R)-1-Methoxy-3-phe...
Compound Q&A

What industries use Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate (CAS: 56649-47-9)?

Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate is used in various industries...

56649-47-9Ethyl 1-(1-phenyleth...
Compound Q&A

What regulatory guidelines apply to 4-[(1E,3S)-1-(4-Hydroxyphenyl)-1,4-pentadien-3-yl]phenol (CAS: 17676-24-3)?

4-[(1E,3S)-1-(4-Hydroxyphenyl)-1,4-pentadien-3-yl]phenol (CAS: 17676-24-3) falls...

17676-24-34-[(1E,3S)-1-(4-Hydr...
Compound Q&A

What industries use (S)-3-Amino-5-phenylpentanoic acid hydrochloride (CAS: 331846-97-0)?

(S)-3-Amino-5-phenylpentanoic acid hydrochloride is primarily used in the pharma...

331846-97-0(S)-3-Amino-5-phenyl...
Compound Q&A

How is 7-methoxy-1-benzothiophene-2-carboxylic acid (CAS: 88791-07-5) typically synthesized?

7-Methoxy-1-benzothiophene-2-carboxylic acid is typically synthesized by reactin...

88791-07-57-methoxy-1-benzothi...

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 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.