Synthesis of Trifluoromethyl-Containing Vicinal Diamines by Asymmetric Decarboxylative Mannich Addition Reactions

被引：36

作者：

Wu, Lingmin ^{[1
]}

Xie, Chen ^{[1
]}

Mei, Haibo ^{[1
]}

Dai, Yanling ^{[1
]}

Han, Jianlin ^{[1
]}

Sooshonok, Vadim A. ^{[2
,3
]}

Pan, Yi ^{[1
]}

机构：

[1] Nanjing Univ, State Key Lab Coordinat Chem, Sch Chem & Chem Engn, Nanjing 210093, Jiangsu, Peoples R China

[2] Univ Basque Country UPV EHU, Dept Organ Chem 1, Fac Chem, San Sebastian 20018, Spain

[3] Basque Fdn Sci, IKERBASQUE, Bilbao 48011, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 06期

基金：

中国国家自然科学基金;

关键词：

GLYCINE SCHIFF-BASES; STEREOSELECTIVE-SYNTHESIS; ALPHA; BETA-DIAMINO ACIDS; AMINATIVE UMPOLUNG; FLUORINE CHEMISTRY; DERIVATIVES; EFFICIENT; ESTERS; IMINES; DIASTEREOSELECTIVITY;

D O I：

10.1021/acs.joc.5b00124

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein is reported a study of asymmetric decarboxylative Mannich addition reactions between (S-s)-N-t-butylsulfinyl-3,3,3-trifluoroacetaldimine and Schiff bases derived from various aldehydes and lithium 2,2-diphenylglycinate. These reactions proceed with excellent diastereoselectivities and good chemical yields, providing a practical method for preparation of trifluoromethyl-containing vicinal diamines. The procedures can be conducted under convenient conditions, rendering this approach of high synthetic value.

引用

页码：3187 / 3194

页数：8

共 50 条

[41] Asymmetric synthesis of vicinal amino alcohols via organocatalytic sequential α-amination/Grignard addition reactions of aldehydes
Liu, Can
Weng, Jiang
Lin, Zi-Hui
Huang, Wei-Jie
Guo, Jing
Huang, Lin-Jie
Lu, Gui
TETRAHEDRON-ASYMMETRY, 2017, 28 (01) : 41 - 46
[42] Synthesis of trifluoromethyl-containing pyrazolidine- and 2-pyrazoline-1-carboxyamides and -thioamides
Sanin, AV
Nenaydenko, VG
Kuzmin, VS
Balenkova, ES
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1998, (05): : 634 - 644
[43] Synthesis and testing of trifluoromethyl-containing phosphonate-peptide conjugates as inhibitors of serine hydrolases
Sokolova, Nadezhda V.
Nenajdenko, Valentine G.
Sokolov, Vladimir B.
Serebryakova, Olga G.
Makhaeva, Galina F.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (23) : 7216 - 7218
[44] New nitrogen containing chiral diselenides: Synthesis and asymmetric addition reactions to olefins
Tiecco, M
Testaferri, L
Santi, C
Tomassini, C
Marini, F
Bagnoli, L
Temperini, A
TETRAHEDRON-ASYMMETRY, 2000, 11 (23) : 4645 - 4650
[45] Diastereoselective Synthesis of Vicinal Diamines by Aza-Michael Addition of Chiral Phenethylamine to Nitroalkenes
Ma, Chunying
Du, Jianxun
Liang, Yuhua
Feng, Wenhua
CHEMISTRYSELECT, 2018, 3 (34): : 9916 - 9919
[46] Convenient enantioselective synthesis of β-trifluoromethyl-β-aminoketones by organocatalytic asymmetric Mannich reaction of aryl trifluoromethyl ketimines with acetone
Sukach, Volodymyr A.
Golovach, Nataliya M.
Pirozhenko, Volodymyr V.
Rusanov, Eduard B.
Vovk, Mykhaylo V.
TETRAHEDRON-ASYMMETRY, 2008, 19 (06) : 761 - 764
[47] Trifluoromethyl-containing pyrazolinyl (p-tolyl) sulfones:: The synthesis and structure of promising antimicrobial agents
Bonacorso, Helio G.
Wentz, Alexandre P.
Lourega, Rogerio V.
Cechinel, Cleber A.
Moraes, Tatiana S.
Coelho, Helena S.
Zanatta, Nilo
Martins, Marcos A. P.
Hoerner, Manfredo
Alves, Sydney H.
JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (08) : 1066 - 1072
[48] New Synthesis of Trifluoromethyl Aldimines Containing L--Amino Ester Moieties and Their Use in Mannich-Type Reactions
Parise, Luca
Pelagalli, Alessia
Trulli, Laura
Vergari, Maria Cecilia
Fioravanti, Stefania
Pellacani, Lucio
CHIRALITY, 2015, 27 (09) : 571 - 575
[49] Synthesis of β-Aminoketones via Arylboronic Acid Catalyzed Decarboxylative Mannich Reactions of Enamines and β-Ketoacids
Wang, Beining
Wang, Yiding
Li, Jun
Zhao, Liuying
Wang, Junyu
Wei, Xinyu
Yuan, Xiangyang
Hu, Haipeng
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 28 (11)
[50] Vinylogous Mannich reactions. The asymmetric total synthesis of (+)-croomine
Martin, SF
Barr, KJ
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (13) : 3299 - 3300

← 1 2 3 4 5 →