Stereoselective Synthesis of Trisubstituted Epoxides Marks the Route to Chiral Building Blocks with Quaternary Centers

被引：4

作者：

Garcia-Castro, Miguel ^{[1
]}

Annamalai, Murali ^{[1
]}

Golz, Christopher ^{[2
]}

Strohmann, Carsten ^{[2
]}

Kumar, Kamal ^{[1
]}

机构：

[1] Max Planck Inst Mol Physiol, Abt Chem Biol, Otto Hahn Str 11, D-44227 Dortmund, Germany

[2] Tech Univ Dortmund, Fak Chem & Chem Biol, Otto Hahn Str 6, D-44221 Dortmund, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 37期

关键词：

Asymmetric synthesis; Epoxidation; Sulfur; Ylides; Ketones; Amino alcohols; CATALYTIC ASYMMETRIC EPOXIDATION; HIGHLY ENANTIOSELECTIVE EPOXIDATION; GLYCIDIC AMIDES; SULFUR YLIDES; SULFONIUM SALTS; AMINO-ACIDS; IN-SITU; ALDEHYDES; KETONES; MECHANISM;

D O I：

10.1002/ejoc.201701148

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile access to enantiomerically pure derivatives of alpha-hydroxy-beta-amino acids bearing a quaternary center and trifluoromethylated tertiary alcohols, which represent highly important building blocks for therapeutically relevant small molecules, has been efficiently achieved by developing an asymmetric epoxidation of alpha-activated ketones by employing chiral sulfur ylides.

引用

页码：5660 / 5665

页数：6

共 50 条

[21] ENANTIOSELECTIVE SYNTHESIS OF POLYFUNCTIONAL SMALL BUILDING-BLOCKS WITH A QUATERNARY STEREOGENIC CENTER
ENDERS, D
ZAMPONI, A
SCHAFER, T
NUBLING, C
EICHENAUER, H
DEMIR, AS
RAABE, G
CHEMISCHE BERICHTE, 1994, 127 (09) : 1707 - 1721
[22] Expedient Dual Co/Organophotoredox Catalyzed Stereoselective Synthesis of All-Carbon Quaternary Centers
Cristofol, Alex
Limburg, Bart
Kleij, Arjan W.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (28) : 15266 - 15270
[23] Catalytic Asymmetric Homologation of α-Ketoesters with α-Diazoesters: Synthesis of Succinate Derivatives with Chiral Quaternary Centers
Li, Wei
Liu, Xiaohua
Tan, Fei
Hao, Xiaoyu
Zheng, Jianfeng
Lin, Lili
Feng, Xiaoming
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (41) : 10883 - 10886
[24] Enantioselective synthesis of quaternary stereogenic centers through catalytic asymmetric addition of dimethylzinc to α-ketoesters with chiral cis-cyclopropane-based amide alcohol as ligand
Zheng, Bing
Hou, Shicong
Li, Zhiyuan
Guo, Hongchao
Zhong, Jiangchun
Wang, Min
TETRAHEDRON-ASYMMETRY, 2009, 20 (18) : 2125 - 2129
[25] Synthesis and configurational assignment of chiral salicylic aldehydes: Novel building blocks for asymmetric catalysis
Berkessel, A
Vennemann, MR
Lex, J
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (16) : 2800 - 2807
[26] Chiral Thiazoline and Thiazole Building Blocks for the Synthesis of Peptide-Derived Natural Products
Just-Baringo, Xavier
Albericio, Fernando
Alvarez, Mercedes
CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2014, 14 (10) : 1244 - 1256
[27] Reductive capabilities of different cyanobacterial strains towards acetophenone as a model substrate - Prospect of applications for chiral building blocks synthesis
Zymanczyk-Duda, Ewa
Glab, Agata
Gorak, Monika
Klimek-Ochab, Magdalena
Brzezinska-Rodak, Malgorzata
Strub, Daniel
Slizewska, Agnieszka
BIOORGANIC CHEMISTRY, 2019, 93
[28] Diastereoselective construction of chiral building blocks for the synthesis of indole alkaloids using an intramolecular Heck reaction
Murakami, Yuri
Yoshida, Masahiro
Shishido, Kozo
TETRAHEDRON LETTERS, 2009, 50 (12) : 1279 - 1281
[29] Phosphonamidates of Camphorsultam: Versatile Building Blocks for the Synthesis of P-Chiral Phosphorous(V) Compounds
Yamamoto, Yasutomo
Kambara, Yurika
Matsumoto, Ayase
Murata, Miku
Nakamoto, Mizuki
Ishiura, Tomoe
Nakai, Sakura
China, Hideyasu
Watanabe, Kenji
Miyawaki, Akari
Matsuoka, Junpei
ADVANCED SYNTHESIS & CATALYSIS, 2025, 367 (03)
[30] Design and Enantioselective Synthesis of β-Vinyl Tryptamine Building Blocks for Construction of Privileged Chiral Indole Scaffolds
Lin, Tao-Yan
Wu, Hai-Hong
Feng, Jian-Jun
Zhang, Junliang
ACS CATALYSIS, 2017, 7 (06): : 4047 - 4052

← 1 2 3 4 5 →