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

被引：25

作者：

Ishii, A

Kanai, M

Higashiyama, K

Mikami, K ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Appl Chem, Tokyo 1528552, Japan

[2] Hoshi Univ, Fac Pharmaceut Sci, Tokyo 142, Japan

来源：

CHIRALITY | 2002年 / 14卷 / 09期

关键词：

4,4,4-trifluoro-3-hydroxybutyrophenone; 4,4,4-trifluoro-3-hydroxybutyrate; homochiral; conglomerate; heterochiral; racemate;

D O I：

10.1002/chir.10040

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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. (C) 2002 Wiley-Liss, Inc.

引用

收藏

页码：709 / 712

页数：4

相关论文

共 24 条

[1] Asymmetric catalytic routes to chiral building blocks of medicinal interest [J].

Burk, MJ ;

Gross, MF ;

Harper, TGP ;

Kalberg, CS ;

Lee, JR ;

Martinez, JP .

PURE AND APPLIED CHEMISTRY, 1996, 68 (01) :37-44

[2] PREPARATION AND REACTIONS OF ETHYL (R,R)-3-TRIFLUOROMETHYLOXIRANE-2-CARBOXYLATE AND (S,S)-3-TRIFLUOROMETHYLOXIRANE-2-CARBOXYLATE, A VERSATILE, EASILY ACCESSIBLE CF3-CONTAINING BUILDING BLOCK FOR SYNTHESIS [J].

BUSSCHEHUNNEFELD, CV ;

SEEBACH, D .

CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05) :1273-1281

[3]

Eliel E.L., 1994, Stereochemistry of Organic Compounds

[4] PREPARATION OF BOTH ENANTIOMERS OF ETHYL 4,4,4-TRIFLUORO-3-HYDROXY BUTANOATE BY ENANTIOSELECTIVE MICROBIAL REDUCTION [J].

GUERRERO, A ;

RAJA, F .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (12) :675-678

[5]

Hiyama T., 2013, ORGANOFLUORINE COMPO

[6] Asymmetric catalytic Friedel-Crafts reaction of silyl enol ethers with fluoral: A possible mechanism of the Mukaiyama-Aldol reactions [J].

Ishii, A ;

Kojima, J ;

Mikami, K .

ORGANIC LETTERS, 1999, 1 (12) :2013-2016

[7]

Jacques J., 1981, Enantiomers, Racemates and Resolutions

[8] Crystal structures of the salts of chiral primary amines with achiral carboxylic acids: Recognition of the commonly-occurring supramolecular assemblies of hydrogen-bond networks and their role in the formation of conglomerates [J].

Kinbara, K ;

Hashimoto, Y ;

Sukegawa, M ;

Nohira, H ;

Saigo, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (14) :3441-3449

[9] ASYMMETRIC REDUCTION OF FLUORINATED KETONES AND KETO ESTERS WITH BAKERS-YEAST [J].

KITAZUME, T ;

YAMAZAKI, T ;

ISHIKAWA, N .

NIPPON KAGAKU KAISHI, 1983, (09) :1363-1368

[10]

Krow G.R., 1993, ORGANIC REACTIONS, V43, P251, DOI DOI 10.1002/0471264180.OR043.03