Nucleophilic substitution of optically active 1-alkoxypolyfluoroalkyl sulfonates

Matsutani, Hiroshi; Poras, Hervé; Kusumoto, Tetsuo; Hiyama, Tetsuo

doi:10.1039/a801847b

Cited by 15 publications

(9 citation statements)

References 13 publications

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“…[62] Alternatively, optically pure 1-alkoxy-2,2,2-ethyl tosylates are accessible by the optical resolution of racemic tosylates by chiral preparative HPLC (Daicel chiralpak AD or chiralcel OD). [63] The presence of the CF 3 group makes it possible to isolate otherwise unstable a-alkoxyalkyl tosylates.…”

Section: Methodsmentioning

confidence: 99%

Modern Synthetic Methods for Fluorine‐Substituted Target Molecules

Shimizu¹,

Hiyama²

2004

Angew Chem Int Ed

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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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Section: Methodsmentioning

confidence: 99%

Modern Synthetic Methods for Fluorine‐Substituted Target Molecules

Shimizu¹,

Hiyama²

2004

Angew Chem Int Ed

Self Cite

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%

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

Katagiri

2002

Chirality

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“…11 According to the methodology presented here, various kinds of optically active 1,1,1-trifluoro-2-alkanols are now available from 1-alkenes, because hydrogenolysis of 6 is easily performed as discussed before. 2 Typical procedure for the reaction of (R)-4 with lithium tetrahexylaluminate (5a). To a diethyl ether ( …”

Section: Methodsmentioning

confidence: 99%