Aminative Umpolung cyclization for synthesis of chiral exocyclic vicinal diamines

Literature Information

Publication Date 2018-09-26
DOI 10.1039/C8OB02000K
Impact Factor 3.876
Authors

Feng Liu, Guoqing Zhao, Weiqi Cai, Dongfang Xu, Baoguo Zhao


View Original

Abstract

Chiral exocylic vicinal diamines are biologically and chemically important compounds, but they are not easy to make. In this paper, an interesting aminative Umpolung cyclization process has been developed. Aromatic aldehydes 6 bearing an electrophilic chiral sulfinimine group underwent imine formation with 2,2-diphenylglycine (2), decarboxylation, and subsequent Umpolung cyclization, producing various trans-diamines 10 in 84–96% yields with high trans/cis ratios under very mild conditions. This work not only provides an efficient, clean, and mild method for the synthesis of chiral exocyclic vicinal diamines in one step but also represents a new application of aminative Umpolung strategy on intramolecular reactions.

Related Literature

Exploring the relationship between cocrystal stability and symmetry: is Wallach's rule applicable to multi-component solids?

Tomislav Friščić, László Fábián, Jonathan C. Burley, David G. Reid, Melinda J. Duer, William Jones

2008-01-30 Communication

DOI: 10.1039/B717532A

Lewis acid-catalyzed hydrogenation: B(C6F5)3-mediated reduction of imines and nitriles with H2‡

Preston A. Chase, Titel Jurca, Douglas W. Stephan

2008-03-06 Communication

DOI: 10.1039/B718598G

Clean and efficient synthesis of O-silylcarbamates and ureas in supercritical carbon dioxide

Matthew J. Fuchter, Catherine J. Smith, Alistair Boyer, Simon Saubern, John H. Ryan, Andrew B. Holmes

2008-04-02 Communication

DOI: 10.1039/B801537F

Recent progress in the immobilization of catalysts for selective oxidation in the liquid phase

Luc Alaerts, Joos Wahlen, Pierre A. Jacobs, Dirk E. De Vos

2008-01-08 Feature Article

DOI: 10.1039/B715691J

Back cover

Front/Back Matter

DOI: 10.1039/B805698F

Fully reversible guest exchange in tetraphosphonate cavitand complexes probed by fluorescence spectroscopy

Elisa Biavardi, Gionata Battistini, Marco Montalti, Roger M. Yebeutchou, Luca Prodi, Enrico Dalcanale

2008-03-05 Communication

DOI: 10.1039/B801729H

Interpenetrating single helical capsules

Emanuela Berni, Joachim Garric, Corinne Lamit, Brice Kauffmann, Jean-Michel Léger, Ivan Huc

2008-02-28 Communication

DOI: 10.1039/B719712H

Template-controlled topochemical photodimerization based on “organometallic macrocycles” through single-crystal to single-crystal transformation

Ying-Feng Han, Yue-Jian Lin, Wei-Guo Jia, Guo-Liang Wang, Guo-Xin Jin

2008-02-11 Communication

DOI: 10.1039/B717554J

Unique intermolecular reaction of simple porphyrins at a metal surface gives covalent nanostructures

Mendel In’t Veld, Patrizia Iavicoli, Sam Haq, David B. Amabilino, Rasmita Raval

2008-02-20 Communication

DOI: 10.1039/B718865J

Synthesis and properties of trifluoroethoxy-coated binuclear phthalocyanine

Hideyuki Yoshiyama, Norio Shibata, Takefumi Sato, Shuichi Nakamura, Takeshi Toru

2008-03-28 Communication

DOI: 10.1039/B800918J

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 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.