Design of New Amino Tf-Amide Organocatalysts: Environmentally Benign Approach to Asymmetric Aldol Synthesis

被引：13

作者：

Lee, Hyo-Jun ^{[1
]}

Arumugam, Natarajan ^{[2
]}

Almansour, Abdulrahman I. ^{[2
]}

Kumar, Raju Suresh ^{[2
]}

Maruoka, Keiji ^{[1
,3
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

[2] King Saud Univ, Coll Sci, Dept Chem, POB 2455, Riyadh 11451, Saudi Arabia

[3] Guangdong Univ Technol, Sch Chem Engn & Light Ind, HEMC, 100 West Waihuan Rd, Guangzhou 510006, Guangdong, Peoples R China

来源：

SYNLETT | 2019年 / 30卷 / 04期

关键词：

asymmetric synthesis; aldol reaction; organocatalyst; brine; Mannich reaction; DIFFERENT PSEUDOENANTIOMERIC ORGANOCATALYSTS; MANNICH REACTIONS; EFFICIENT ORGANOCATALYST; PRACTICAL SYNTHESIS; SULFONAMIDE; ALDEHYDES; WATER;

D O I：

10.1055/s-0037-1610408

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new type of optically pure primary amino aromatic Tf-amide organocatalyst can be easily prepared from 8-amino-1-tetralone, and its chemical behavior was investigated in the context of asymmetric aldol and Mannich reactions. Most notably, the asymmetric aldol reaction proceeded smoothly in brine.

引用

页码：401 / 404

页数：4

共 47 条

[41] A new synthesis of enantiomerically pure syn-(S)-β-hydroxy-α-amino acids via asymmetric aldol reactions of aldehydes with a homochiral Ni(II)-glycine/(S)-BPB Schiff base complex
Belokon, YN
Kochetkov, KA
Ikonnikov, NS
Strelkova, TV
Harutyunyan, SR
Saghiyan, AS
TETRAHEDRON-ASYMMETRY, 2001, 12 (03) : 481 - 485
[42] Design and synthesis of new classes of Heterocyclic C-glycoconjugates and carbon-linked sugar and heterocyclic amino acids by asymmetric multicomponent reactions (AMCRs)
Dondoni, Alessandro
Massi, Alessandro
ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (07) : 451 - 463
[43] Isoxazolinium salts in asymmetric synthesis.: 1.: Stereoselective reduction induced by a 3'-alkoxy stereocentre.: A new approach to polyfunctionalized β-amino acids
Henneböhle, M
Le Roy, PY
Hein, M
Ehrler, R
Jäger, V
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2004, 59 (04): : 451 - 467
[44] ORGN 117-Synthesis of a new, non-natural amino acid based on (1R, 3S) camphoric acid and its application as an asymmetric organocatalyst in the direct aldol condensation
Eagles, Joel B.
Hitchcock, Shawn R.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237
[45] ASYMMETRIC [1, 3]-PROTON SHIFT IN AZOMETHINES AS A NEW APPROACH TO SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-TRIFLUOROMETHYL CONTAINING AMINES AND AMINO-ACIDS
KUKHAR, VP
SOLOSHONOK, VA
GALUSHKO, SV
ROZHENKO, AB
DOKLADY AKADEMII NAUK SSSR, 1990, 310 (04): : 886 - 889
[46] AMINO-ACIDS AND PEPTIDES .13. NEW APPROACH TO BIOGENETIC-TYPE, ASYMMETRIC SYNTHESIS OF INDOLE AND ISOQUINOLINE ALKALOIDS BY 1,3-TRANSFER OF ASYMMETRY
AKIMOTO, H
OKAMURA, K
YUI, M
SHIOIRI, T
KURAMOTO, M
KIKUGAWA, Y
YAMADA, SI
CHEMICAL & PHARMACEUTICAL BULLETIN, 1974, 22 (11) : 2614 - 2623
[47] A NEW SYNTHETIC APPROACH TO PSEUDO-SUGARS BY ASYMMETRIC DIELS-ALDER REACTION - SYNTHESIS OF OPTICALLY PURE PSEUDO-BETA-D-MANNOPYRANOSE, 1-AMINO-1-DEOXYPSEUDO-ALPHA-D-MANNOPYRANOSE AND PSEUDO-ALPHA-L-MANNOPYRANOSE DERIVATIVES
TAKAHASHI, T
KOTSUBO, H
IYOBE, A
NAMIKI, T
KOIZUMI, T
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11): : 3065 - 3072

← 1 2 3 4 5 →