Catalytic enantioselective one-pot approach to cis- and trans-2,3-diaryl substituted 1,5-benzothiazepines

Literature Information

Publication Date 2018-09-12
DOI 10.1039/C8OB01988F
Impact Factor 3.876
Authors

Sara Meninno, Ilaria Quaratesi, Chiara Volpe, Andrea Mazzanti, Alessandra Lattanzi


View Original

Abstract

The first enantioselective catalytic approach to cis- and trans-2,3-diaryl substituted 1,5-benzothiazepines has been conveniently developed in a one-pot fashion, starting from α,β-unsaturated acyl pyrazoles and 2-aminothiophenol. The organocatalytic two-step sulfa-Michael/lactamization sequence is promoted by a readily available bifunctional thiourea and p-toluenesulfonic acid, respectively. The protocol enables access to both N-unprotected cis- and trans-diastereoisomers in moderate to satisfactory overall yields (up to 84%) and good to excellent ee values (up to 99%). Mechanistic investigations helped to shed light on the regio- and stereoselective outcome of the process.

Related Literature

A new insight into the nanostructure of alkylammonium alkanoates based ionic liquids in water

Umme Salma, Paolo Ballirano, Marianna Usula, Ruggero Caminiti, Natalia V. Plechkova, Kenneth R. Seddon, Lorenzo Gontrani

2016-03-21 Paper

DOI: 10.1039/C5CP07953E

Thermoelectric transport properties of pristine and Na-doped SnSe1−xTex polycrystals

Tian-Ran Wei, Chao-Feng Wu, Xiaozhi Zhang, Qing Tan, Li Sun, Yu Pan, Jing-Feng Li

2015-10-15 Paper

DOI: 10.1039/C5CP05510E

Biexponential photon antibunching: recombination kinetics within the Förster-cycle in DMSO

Michael Vester, Andreas Grueter, Björn Finkler, Robert Becker, Gregor Jung

2016-03-11 Paper

DOI: 10.1039/C6CP00718J

Photo-induced oxidation of the uniquely liganded heme f in the cytochrome b6f complex of oxygenic photosynthesis

Adrien A. P. Chauvet, Rachna Agarwal, André al Haddad, Frank van Mourik, William A. Cramer

2016-04-19 Paper

DOI: 10.1039/C6CP01592A

The interactions between TiO2 and graphene with surface inhomogeneity determined using density functional theory

Brandon Bukowski, N. Aaron Deskins

2015-10-12 Paper

DOI: 10.1039/C5CP04073F

Ab initio energy loss spectra of Si and Ge nanowires

Stefano Ossicini

2015-10-06 Paper

DOI: 10.1039/C5CP05074J

A designed lipopeptide with a leucine zipper as an imbedded on/off switch for lipid bilayers

Sijia Wang, Yinxing Shen, Junqi Zhang, Shouhong Xu, Honglai Liu

2016-03-11 Paper

DOI: 10.1039/C6CP00378H

You might also like

Compound Q&A

What is the market or research trend for N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0)?

N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0) is increasingly being used ...

52818-63-0N-(4-Methoxybenzyl)-...
Compound Q&A

What precautions should be taken when handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate (CAS: 1050507-06-6)?

When handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate, appropriate p...

1050507-06-6Ethyl 4-(2-chlorophe...
Compound Q&A

What regulatory guidelines apply to diethyldiselane (CAS: 628-39-7)?

Diethyldiselane (CAS: 628-39-7) is classified under the Globally Harmonized Syst...

628-39-7Diethyldiselane
Compound Q&A

What is the market or research trend for oxocopper (CAS: 12053-18-8)?

The market for oxocopper (CAS: 12053-18-8) is primarily driven by its use in cat...

12053-18-8oxocopper; oxo-(oxoc...
Compound Q&A

What is the market or research trend for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-carboxylic acid?

The market for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-c...

1268519-54-55-{[(2-Methyl-2-prop...
Compound Q&A

What is 2-(1-Pyrrolidinyl)-4-pyridinamine (CAS: 35981-63-6)?

2-(1-Pyrrolidinyl)-4-pyridinamine is a chemical compound with the CAS number 359...

35981-63-62-(1-Pyrrolidinyl)-4...
Compound Q&A

What are the physical and chemical properties of 2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1)?

2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1) is a crystalline sol...

91556-75-12-(3-Pyridinyl)-1-az...
Compound Q&A

How is (S)-Alpha-allyl-proline hydrochloride (CAS: 129704-91-2) typically synthesized?

(S)-Alpha-allyl-proline hydrochloride is usually synthesized via a Wittig reacti...

129704-91-2(S)-Alpha-allyl-prol...
Compound Q&A

What is 3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5)?

3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5) is an organic compound w...

4857-42-53-Methyl-1,2-oxazole...
Compound Q&A

How is Lys-SMCC-DM1 (CAS: 1281816-04-3) typically synthesized?

Lys-SMCC-DM1 is synthesized via a multi-step process involving the coupling of S...

1281816-04-3Lys-SMCC-DM1

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.