Intramolecular SN2 reaction at α-carbon of trifluoromethyl group: preparation of optically active 2-trifluoromethylaziridine

Fluorine has come to be recognized as a key element in materials science: in heat-transfer agents, liquid crystals, dyes, surfactants, plastics, elastomers, membranes, and other materials. Furthermore, many fluorine-containing biologically active agents are finding applications as pharmaceuticals and agrochemicals. Progress in synthetic fluorine chemistry has been critical to the development of these fields and has led to the invention of many novel fluorinated molecules as future drugs and materials. As a result of the electronic effects of fluorine substituents, fluorinated substrates and reagents often exhibit unusual and unique chemical properties, which often make them incompatible with established synthetic methods. Thus, the problem of how to control the unusual properties of compounds with fluorine substituents deserves much attention, so as to promote the design of facile, efficient, and environmentally benign methods for the synthesis of valuable organofluorine targets.

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“…[65] The versatility of the present approach is demonstrated by the preparation of 1,1,1-trifluoro-2-alkanols (Scheme 33).…”

Section: Methodsmentioning

confidence: 98%

Modern Synthetic Methods for Fluorine‐Substituted Target Molecules

Shimizu¹,

Hiyama²

2004

Angew Chem Int Ed

800

170

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“…Recent progress in the stereospecific substitution reactions of the hydroxy groups, [39][40][41]53,57,58,[60][61][62][63][64][65][66][67][68][69] as well as the versatile construction of optically active CF 3 -CH(OH)-unit continues to improve the reliability and availability of the optically active trifluoromethylated compounds.…”

Section: Resultsmentioning

confidence: 99%

“…39 The stereochemistry of the aziridine was confirmed to be (R); the reaction was also completed with complete inversion of configuration.…”

Section: -Trifluoromethyl Aziridine a General Precursor For ␣-Triflmentioning

confidence: 91%

“…We believed that the Coulombic repulsion effect would be suppressed somewhat in an intramolecular substitution, because a nucleophile would be readily put near the reaction center. In fact, we succeeded in preparing optically active aziridine 39 and cyclopropanes 40,41 via the intramolecular nucleophilic substitutions of the hydroxy group in the CF 3 -CH(OH)-unit.…”

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confidence: 99%

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Stereospecific substitution at α‐carbon to trifluoromethyl group: Application to optically active fluorinated amino acid syntheses

Katagiri

2002

Chirality

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“…In some cases the conversion of alicyclic epoxy compounds 123 resulted in the formation of hydroxyl containing framework amines 124, 125 or their acyl forms 126, 127 (Scheme 43) [126].…”

Section: Heterocyclization Of Epoxide Derivatives Of Framework Aminesmentioning

confidence: 99%