Economy of Catalyst Synthesis—Convenient Access to Libraries of Di- and Tetranaphtho Azepinium Compounds

Tharamak, Sorachat; Knittl-Frank, Christian; Manaprasertsak, Auraya; Pengsook, Anchulee; Suchy, Lydia; Schuller, Philipp; Happl, Barbara; Roller, Alexander; Widhalm, Michael

doi:10.3390/molecules23040750

Open AccessFeature PaperArticle

Economy of Catalyst Synthesis—Convenient Access to Libraries of Di- and Tetranaphtho Azepinium Compounds

by

Sorachat Tharamak

¹,

Christian Knittl-Frank

²

,

Auraya Manaprasertsak

¹,

Anchulee Pengsook

¹,

Lydia Suchy

²,

Philipp Schuller

²,

Barbara Happl

³,

Alexander Roller

³ and

Michael Widhalm

^4,*

¹

Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand

²

Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, Wien 1090, Austria

³

Institute of Inorganic Chemistry, University of Vienna, Währinger Straße 42, Wien 1090, Austria

⁴

Institute of Chemical Catalysis, University of Vienna, Währinger Straße 38, Wien 1090, Austria

^*

Author to whom correspondence should be addressed.

Molecules 2018, 23(4), 750; https://doi.org/10.3390/molecules23040750

Submission received: 22 February 2018 / Revised: 14 March 2018 / Accepted: 20 March 2018 / Published: 24 March 2018

(This article belongs to the Special Issue Enantioselective Catalysis)

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Abstract

Efficient optimization procedures in chiral catalysis are usually linked to a straightforward strategy to access groups of structurally similar catalysts required for fine-tuning. The ease of building up such ligand libraries can be increased when the structure-modifying step (introduction of a substituent) is done at a later stage of the synthesis. This is demonstrated for the extended family of di- and tetranaphtho azepinium compounds, widely used as chiral phase transfer catalysts (PTC). Using 2,6-diiodo-4,5-dihydro-3H-dinaphtho[2,1-c:1′,2′-e]azepine and 4,8-diiodo-6,7-dihydro-5H-dibenzo[c,e]azepine, respectively, as key intermediates, 18 spiro-azepinium compounds were synthesized in a total yield of 25–42% over 6–7 steps from 1,1′-binaphthyl-2,2′-dicarboxylic acid or diphenic acid, respectively. The replacement of iodo groups with aryl substituents was performed as the last or the penultimate step of the synthesis.

Keywords: 1,1′-binaphthyl; biphenyl; Suzuki-Miyaura coupling; phase transfer catalyst

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MDPI and ACS Style

Tharamak, S.; Knittl-Frank, C.; Manaprasertsak, A.; Pengsook, A.; Suchy, L.; Schuller, P.; Happl, B.; Roller, A.; Widhalm, M. Economy of Catalyst Synthesis—Convenient Access to Libraries of Di- and Tetranaphtho Azepinium Compounds. Molecules 2018, 23, 750. https://doi.org/10.3390/molecules23040750

AMA Style

Tharamak S, Knittl-Frank C, Manaprasertsak A, Pengsook A, Suchy L, Schuller P, Happl B, Roller A, Widhalm M. Economy of Catalyst Synthesis—Convenient Access to Libraries of Di- and Tetranaphtho Azepinium Compounds. Molecules. 2018; 23(4):750. https://doi.org/10.3390/molecules23040750

Chicago/Turabian Style

Tharamak, Sorachat, Christian Knittl-Frank, Auraya Manaprasertsak, Anchulee Pengsook, Lydia Suchy, Philipp Schuller, Barbara Happl, Alexander Roller, and Michael Widhalm. 2018. "Economy of Catalyst Synthesis—Convenient Access to Libraries of Di- and Tetranaphtho Azepinium Compounds" Molecules 23, no. 4: 750. https://doi.org/10.3390/molecules23040750

APA Style

Tharamak, S., Knittl-Frank, C., Manaprasertsak, A., Pengsook, A., Suchy, L., Schuller, P., Happl, B., Roller, A., & Widhalm, M. (2018). Economy of Catalyst Synthesis—Convenient Access to Libraries of Di- and Tetranaphtho Azepinium Compounds. Molecules, 23(4), 750. https://doi.org/10.3390/molecules23040750

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Economy of Catalyst Synthesis—Convenient Access to Libraries of Di- and Tetranaphtho Azepinium Compounds

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