protocol-for-synthesis-ortho-trifluoromethoxylated-aniline

Protocol for the Synthesis of <em>Ortho</em>-trifluoromethoxylated Aniline Derivatives

Molecules bearing trifluoromethoxy (OCF3) group often show desired pharmacological and biological properties. However, facile synthesis of ...

State University of New York at Stony Brook

A rapid approach to the skeleton of dalesconol A and B, unprecedented immunosuppressants, has been achieved through a convergent strategy featuring a carbocation-mediated dearomatization-cyclization and a following one-pot consecutive operation.

A concise approach to the dalesconol skeleton.

A strategy to construct the hexacyclic skeleton of trigonoliimines A, B and their derivatives involving a carbanion-triggered intramolecular cyclization of a seven-membered ring and a subsequent six-membered ring formation in one pot is described.

An approach to the hexacyclic skeleton of trigonoliimines.

An efficient stereoselective approach to the tetracyclic core of Cryptotrione, involving an asymmetric Michael addition, ring-closing metathesis, and subsequent cyclopropanation, is described.

Stereoselective construction of the tetracyclic core of Cryptotrione.

A concise approach to the spiroiminal fragment of marineosins A and B is described. The key steps involve an acid-catalyzed N-acyliminium ion cyclization and a Vilsmeier-Haack type reaction with Tf2O.

A concise approach to the spiroiminal fragment of marineosins.

An approach to the pentacyclic core of aspidophylline A is described. The strategy features CAN-mediated intramolecular azidoalkoxylation of enecarbamate and ruthenium-catalyzed atom transfer cyclization.

An approach to the skeleton of aspidophylline A.

Aryl trifluoromethoxylation by a two-step sequence of O-trifluoromethylation of N-aryl-N-hydroxylamine derivatives and intramolecular OCF3  migration is presented. This protocol allows easy access to a wide range of synthetically useful ortho-OCF3 aniline derivatives. In addition, it utilizes bench-stable reagents, is operationally simple, shows high functional-group tolerance, and is amenable to gram-scale as well as one-pot synthesis. A reaction mechanism of a heterolytic cleavage of the NOCF3 bond followed by recombination of the resulting nitrenium ion and trifluoromethoxide is proposed for the OCF3 -migration reaction.

Article	Year
A concise approach to the dalesconol skeleton. Organic letters\| PubMed ID: 21806037	2011
An approach to the hexacyclic skeleton of trigonoliimines. Organic letters\| PubMed ID: 21988530	2011
Stereoselective construction of the tetracyclic core of Cryptotrione. Organic & biomolecular chemistry\| PubMed ID: 22717843	2012
A concise approach to the spiroiminal fragment of marineosins. Organic & biomolecular chemistry\| PubMed ID: 23535777	2013
An approach to the skeleton of aspidophylline A. Organic letters\| PubMed ID: 23697342	2013
Trifluoromethoxylation of arenes: synthesis of ortho-trifluoromethoxylated aniline derivatives by OCF3 migration. Angewandte Chemie (International ed. in English)\| PubMed ID: 25358501	2014

Pengju Feng

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