An Efficient Method of Preparing (R)- and (S)-4,4,4-Trifluoro9-3-hydroxybutanoic Acid: Resolution with (R)- or (S)-1-Phenylethylamine | Zendy

Mária Ács | Zendy; Christoph Von dem Bussche | Zendy; Dieter Seebàch | Zendy

Open Access

An Efficient Method of Preparing (R)- and (S)-4,4,4-Trifluoro9-3-hydroxybutanoic Acid: Resolution with (R)- or (S)-1-Phenylethylamine

Author(s) -

Mária Ács,

Christoph Von dem Bussche,

Dieter Seebàch

Publication year - 1990

Publication title -

chimia international journal for chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.387

H-Index - 55

eISSN - 2673-2424

pISSN - 0009-4293

DOI - 10.2533/chimia.1990.90

Subject(s) - chemistry , enantiomer , resolution (logic) , enantioselective synthesis , chirality (physics) , stereochemistry , enantiomeric excess , chromatography , organic chemistry , catalysis , chiral symmetry , quantum mechanics , artificial intelligence , quark , nambu–jona lasinio model , physics , computer science

Two crystallizations of the unlike salts 2 from 4,4,4-trif1uoro-3-hydroxybutanoic acid (1) and 1-phenylethylamine, followed by recovery of the free acid, lead to the isolation, in ca. 30% (60% of the theoretical amount), of the (R)- and (S)-acid 1 (m.p. 44°) in ? 98 % enantiomeric excess. The purity of 1 was determined by Mosher's method,and the sense of chirality (+)-(R) and (?)-(S) determined by chemical correlation. The resolution procedure leading to enantiomerically pure 1 is compared with the methods using enzymatic or microbial enantioselective reactions.

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