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Practical asymmetric synthetic route to 4,4,4‐trifluoro‐3‐hydroxybutyrate: Head‐to‐tail and head‐to‐head crystallizations through double and single hydrogen bonds of hetero‐ and homochiral 4,4,4‐trifluoro‐3‐hydroxybutyrophenones
Author(s) -
Ishii Akihiro,
Kanai Masatomi,
Higashiyama Kimio,
Mikami Koichi
Publication year - 2002
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10040
Subject(s) - chemistry , chirality (physics) , hydrogen bond , head (geology) , crystallization , stereocenter , stereochemistry , double bond , butyric acid , enantioselective synthesis , crystallography , catalysis , combinatorial chemistry , organic chemistry , molecule , physics , chiral symmetry breaking , quantum mechanics , geomorphology , nambu–jona lasinio model , quark , geology
A practical asymmetric synthetic route to 4,4,4‐trifluoro‐3‐hydroxybutyrophenone and the butyric acid phenyl ester is described using heterochiral crystallization through double hydrogen bonding assembly in head‐to‐tail fashion and sequential Baeyer‐Villiger oxidation reaction by trifluoroperacetic acid. Chirality 14:709–712, 2002. © 2002 Wiley‐Liss, Inc.