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

[31] Design, Synthesis, Bioactivity Evaluation, Crystal Structures, and In Silico Studies of New α-Amino Amide Derivatives as Potential Histone Deacetylase 6 Inhibitors
Xu, Yangrong
Tang, Hangjun
Xu, Yijie
Guo, Jialin
Zhao, Xu
Meng, Qingguo
Xiao, Junhai
MOLECULES, 2022, 27 (10):
[32] Chiral salen -: Aluminum complexes as catalysts for enantioselective aldol reactions of aldehydes and 5-alkoxyoxazoles:: An efficient approach to the asymmetric synthesis of syn and anti β-hydroxy-α-amino acid derivatives
Evans, DA
Janey, JM
Magomedov, N
Tedrow, JS
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (10) : 1884 - 1888
[33] Catalytic enantio- and diastereoselective aldol reactions of glycine-derived silicon enolate with aldehydes:: An efficient approach to the asymmetric synthesis of anti-β-hydroxy-α-amino acid derivatives
Kobayashi, J
Nakamura, M
Mori, Y
Yamashita, Y
Kobayashi, S
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) : 9192 - 9193
[34] Catalytic enantio- and diastereoselective aldol reactions of glycine-derived silicon enolate with aldehydes: An efficient approach to the asymmetric synthesis of anti-β-hydroxy-α-amino acid derivatives
1600, American Chemical Society, Columbus, United States (126):
[35] Problem Solving and Environmentally Benign Approach toward Diversity Oriented Synthesis of Novel 2-Amino-3-phenyl (or Alkyl) Sulfonyl-4H-chromenes at Ambient Temperature
Pandit, Kapil S.
Kupwade, Ravindra V.
Chavan, Pramod V.
Desai, Uday V.
Wadgaonkar, Prakash P.
Kodam, Kisan M.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2016, 4 (06): : 3450 - 3464
[36] STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES - A NEW APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-HYDRAZINO AND ALPHA-AMINO-ACID DERIVATIVES
EVANS, DA
BRITTON, TC
DOROW, RL
DELLARIA, JF
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) : 6395 - 6397
[37] New approach to aphidicolin and total asymmetric synthesis of unnatural (11R)-(-)-8-epi-11-hydroxyaphidicolin by tandem transannular Diels-Alder/aldol reactions
Bélanger, G
Deslongchamps, P
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21): : 7070 - 7074
[38] ASYMMETRIC ALKYLATION OF CHIRAL BETA-LACTAM ESTER ENOLATES - A NEW APPROACH TO THE SYNTHESIS OF ALPHA-ALKYLATED ALPHA-AMINO-ACIDS
OJIMA, I
QIU, XG
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (21) : 6537 - 6538
[39] A New Approach to Obtaining Nα-t-Boc-Amino Acid Aldehydes from Asparagine and Glutamine for Reduced Amide Pseudopeptide Solid-Phase Synthesis
Carreno, Luisa F.
Alba, Martha P.
Varela, Yahson
Patarroyo, Manuel E.
Manuel Lozano, Jose
CHEMICAL BIOLOGY & DRUG DESIGN, 2011, 78 (04) : 603 - 611
[40] GOLD(I)-CATALYZED ASYMMETRIC ALDOL REACTION OF N-METHOXY-N-METHYL-ALPHA-ISOCYANOACETAMIDE (ALPHA-ISOCYANO WEINREB AMIDE) - AN EFFICIENT SYNTHESIS OF OPTICALLY-ACTIVE BETA-HYDROXY-ALPHA-AMINO ALDEHYDES AND KETONES
SAWAMURA, M
NAKAYAMA, Y
KATO, T
ITO, Y
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06): : 1727 - 1732

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