Synthesis of (S)-2-{(R)-Hydroxy[2-(trifluoromethyl)phenyl]methyl}cyclohexan-1-one Using (1R,2R)-2-(Piperidin-1-yl)cyclohexan-1-amine as a Catalyst

被引：0

作者：

Li, C. L. ^{[1
,2
,3
]}

Wang, S. Y. ^{[1
]}

Zhan, M. R. ^{[1
]}

Chen, C. C. ^{[1
]}

Wang, Z. X. ^{[1
]}

机构：

[1] North Minzu Univ, Sch Chem & Chem Engn, Yinchuan 750021, Peoples R China

[2] North Minzu Univ, Ningxia Key Lab Solar Chem Convers Technol, Yinchuan 750021, Peoples R China

[3] North Minzu Univ, Key Lab Chem Engn & Technol, State Ethn Affairs Commiss, Yinchuan 750021, Peoples R China

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 60卷 / 10期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; cyclohexanediamine catalyst; aldol reaction; organocatalyst; ASYMMETRIC MICHAEL ADDITION;

D O I：

10.1134/S1070428024100166

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral monosubstituted cyclohexanediamine catalyst, namely (1R,2R)-2-(piperidin-1-yl)cyclohexan-1-amine (Cat1) has been efficiently synthesized and used to catalyze the aldol reaction of cyclohexanone and 2-(trifluoromethyl)benzaldehyde to obtain (R)-2-{(S)-hydroxy[2-(trifluoromethyl)phenyl]methyl}cyclohexan-1-one. The catalyst (20 mol %) provided high yield (up to 85%) and excellent enantioselectivity (95.6% ee) in water solution in three parallel tests.

引用

页码：1999 / 2003

页数：5

共 36 条

[21] A Common Approach for the Synthesis of (R)-Ethyl 2,4-dihydroxy-6-(8-hydroxynonyl) benzoate, Ethyl 2,4-Dihydroxy-6-nonylbenzoate and (2R,3R)-1,2,3,4-Butanetetraol-1,4-diorsellinate
Mali, Prakash R.
Chirke, Sahadev S.
Meshram, Harshadas M.
CHEMISTRYSELECT, 2017, 2 (33): : 10718 - 10721
[22] Synthesis of 4-hydroxy-3-benzoylpyridin-2(1H)-one derivatives using pyrrolidine as catalyst
Li, Linbo
Liu, Yuxiao
Zhou, Shujing
Li, Jinjing
Qi, Chenze
Zhang, Furen
SYNTHETIC COMMUNICATIONS, 2023, 53 (06) : 492 - 502
[23] Efficient biosynthesis of(S)-1-[2-(trifluoromethyl)phenyl]ethanol by a novel isolate Geotrichum silvicola ZJPH1811 in deep eutectic solvent/ cyclodextrin-containing system
Xiong, Lilu
Kong, Xiangxin
Liu, Hanyu
Wang, Pu
BIORESOURCE TECHNOLOGY, 2021, 329
[24] Synthesis and characterization of (5R,6R)-6-Pheny1-5-(phenyl-sulfonylacetyl)bicyclo[2.2.1]hept-2-ene
Pei, Wen
Sun, Li
Wang, Hai-Bin
Wang, Yong-Jiang
Shao, Yue-Shui
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2006, 26 (05) : 727 - 729
[25] A short and facile synthesis of 2-(1Z)-(3-hydroxy-3,7-dimethylocta-1,6-dienyl)-1,4-benzenediol and 1-(3'-methoxypropanoyl)-2,4,5-trimethoxybenzene isolated from Cordia alliodora
Kaur, Sukhbir
Singh, Vasundhara
Kumar, Gulshan
Kad, G. L.
Singh, Jasvinder
NATURAL PRODUCT RESEARCH, 2010, 24 (05) : 440 - 447
[26] 1,3-bis[N-sulfonyl-(1R,2S)-1,3-diphenyl-2-aminopropanol]benzene:: An excellent ligand for titanium-catalyzed asymmetric AlPh3(THF) additions to aldehydes
Hsieh, Sheng-Hsiang
Chen, Chien-An
Chuang, Da-Wei
Yang, Mao-Chih
Yang, Hsu-Tang
Gau, Han-Mou
CHIRALITY, 2008, 20 (08) : 924 - 929
[27] Copper(II) complexes containing chiral substituted 2-(4-isopropyl-4-methyl-4,5-dihydro-1H-imidazol-5-one-2-yl)pyridine ligands:: Synthesis, X-ray structural studies and asymmetric catalysis
Sedlak, Milos
Drabina, Pavel
Keder, Roman
Hanusek, Jiri
Cisarova, Ivana
Ruzicka, Ales
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (12) : 2623 - 2630
[28] Novel cyclic 1,2-diacetals derived from (2R,3R)-(+)-tartaric acid:: Synthesis and application as N,O ligands for the enantioselective alkylation of benzaldehyde by diethylzinc
Barros, MT
Maycock, CD
Phillips, AMF
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (08) : 1820 - 1829
[29] An efficient synthetic approach towards a single diastereomer of (2R,3R)-N2,N3-bis((S)-1-phenylethyl)butane-2,3-diamine via metalation and demetalation
Cho, Juhyun
Nayab, Saira
Jeong, Jong Hwa
TRANSITION METAL CHEMISTRY, 2020, 45 (01) : 9 - 17
[30] Direct Asymmetric Aldol Reactions Promoted by (1R, 3S, 4S)-2-Aza-bicyclo[2.2.1]heptane-3-carboxylic Acid as an Organocatalyst
Chen, Wei-Yi
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (01) : 378 - 380

← 1 2 3 4 →