Asymmetric Synthesis of α-Chloro-α-halo Ketones by Decarboxylative Chlorination of α-Halo-β-ketocarboxylic Acids

被引：14

作者：

Kitahara, Kazumasa ^{[1
]}

Mizutani, Haruna ^{[1
]}

Iwasa, Seiji ^{[1
]}

Shibatomi, Kazutaka ^{[1
]}

机构：

[1] Toyohashi Univ Technol, Dept Appl Chem & Life Sci, 1-1 Hibarigaoka,Tempaku Cho, Toyohashi, Aichi 4418580, Japan

来源：

SYNTHESIS-STUTTGART | 2019年 / 51卷 / 23期

关键词：

decarboxylative chlorination; chiral amine catalyst; enantio-selective synthesis; beta-ketocarboxylic acids; fluorinated compounds; QUATERNARY STEREOGENIC CENTERS; ENANTIOSELECTIVE FLUORINATION; CONSTRUCTION; ESTERS; KETOESTERS; LIGANDS;

D O I：

10.1055/s-0039-1690009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral alpha-chloro-alpha-fluoro ketones were synthesized by enantio-selective decarboxylative chlorination of alpha-chloro-beta-ketocarboxylic acids in the presence of a chiral amine catalyst. The reaction yielded the corresponding alpha-chloro-alpha-fluoro ketones with moderate-to-high enantioselectivity (up to 90% ee). The method was also applied to the synthesis of alpha-bromo-alpha-chloro ketones with 90% ee.

引用

页码：4385 / 4392

页数：8

共 50 条

[21] α-halo boronic esters in asymmetric synthesis
Matteson, DS
TETRAHEDRON, 1998, 54 (36) : 10555 - 10606
[22] Enediolates of carboxylic acids in synthesis:: Synthesis of γ-chloro-β-hydroxy acids
Gil, S
Knecteman, M
Parra, M
Sotoca, E
SYNTHESIS-STUTTGART, 2002, (02): : 265 - 273
[23] Selective synthesis of alpha-halo ketones
Toy, Patrick
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
[24] Biocatalyzed Enantioselective Reduction of Activated C=C Bonds: Synthesis of Enantiomerically Enriched α-Halo-β-arylpropionic Acids
Brenna, Elisabetta
Gatti, Francesco G.
Manfredi, Alessia
Monti, Daniela
Parmeggiani, Fabio
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (20-21) : 4015 - 4022
[25] Uncoupling Effect of Fatty Acids in Halo- and Alkalotolerant Bacterium Bacillus pseudofirmus FTU
I. V. Popova
M. E. Bodrova
E. N. Mokhova
M. S. Muntyan
Biochemistry (Moscow), 2004, 69 : 1165 - 1169
[26] Synthesis, antitumoral and antiviral evaluation of halo- and demethyl-yatein derivatives
Medarde, M
deClairac, RPL
Lopez, JL
Gravalos, DG
SanFeliciano, A
ARCHIV DER PHARMAZIE, 1995, 328 (09) : 640 - 644
[27] Synthesis, Characterization, Cytotoxicity, and Antibacterial Properties of trans-γ-Halo-δ-lactones
Kamizela, Angelika
Gawdzik, Barbara
Urbaniak, Mariusz
Lechowicz, Lukasz
Bialonska, Agata
Gonciarz, Weronika
Chmiela, Magdalena
CHEMISTRYOPEN, 2018, 7 (07): : 543 - 550
[28] Uncoupling effect of fatty acids in halo- and alkalotolerant bacterium Bacillus pseudofirmus FTU
Popova, IV
Bodrova, ME
Mokhova, EN
Muntyan, MS
BIOCHEMISTRY-MOSCOW, 2004, 69 (10) : 1165 - 1169
[29] Vanadium-Catalyzed Coupling of Allenols with Electrophilic Halide Sources for the Formation of α-Halo-α′,β′-unsaturated Ketones
Trost, Barry M.
Tracy, Jacob S.
Yusoontorn, Tas
ORGANIC LETTERS, 2019, 21 (04) : 1207 - 1211
[30] SUBSTITUTED ARYLAMIDES OF DITHIOCARBOXYLIC ACIDS .2. SYNTHESIS OF HALO-, SULFO-, AND CARBOXY-N-PHENYLDITHIOOXAMIDES
GRABENKO, AD
PELKIS, PS
JOURNAL OF GENERAL CHEMISTRY USSR, 1961, 31 (08): : 2557 - &

← 1 2 3 4 5 →