Absolute Asymmetric Synthesis of Tertiary a-Amino Acids

被引：21

作者：

Thi Thoa Mai ^{[1
]}

Branca, Mathieu ^{[1
]}

Gori, Didier ^{[1
]}

Guillot, Regis ^{[1
]}

Kouklovsky, Cyrille ^{[1
]}

Alezra, Valerie ^{[1
]}

机构：

[1] Univ Paris 11, Lab Chim Procedes & Subst Nat, CNRS, ICMMO,UMR 8182, F-91405 Orsay, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 20期

关键词：

amino acids; amides; asymmetric synthesis; chirality; synthetic methods; ENANTIOSELECTIVE SYNTHESIS; CHIRAL CRYSTALLIZATION; MOLECULAR CHIRALITY; OPTICAL-ACTIVITY; AROMATIC AMIDES; MEMORY; HOMOLOGATION; GENERATION; ROTATION; ACCESS;

D O I：

10.1002/anie.201200950

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Frozen: The spontaneous crystallization of an achiral compound in a chiral conformation is used as the unique source of chirality in an absolute asymmetric synthesis of tertiary amino acids. The dynamic axial chirality of tertiary aromatic amides is frozen in a crystal (see picture) and is responsible for the stereoselectivity of the deprotonation/alkylation (see scheme). α-Amino acid derivatives are synthesized in up to 96% ee. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4981 / 4984

页数：4

共 50 条

[21] Recent Advances in the Synthesis of Fluorinated Amino Acids
Qiu, Xiao-Long
Qing, Feng-Ling
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (18) : 3261 - 3278
[22] New advances in the asymmetric synthesis of α-amino acids
Jun, Lin
Hui-Dan, Fan
Sheng-Jiao, Yan
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2007, 27 (08) : 925 - 936
[23] Recent development in asymmetric synthesis of β-amino acids
Ma, ZH
Zhao, YH
Wang, JB
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2002, 22 (11) : 807 - 816
[24] Strategies for Asymmetric Synthesis of Amino Acids with γ,δ-Unsaturation
Liu, Zhihua
Mehta, Sukeshi J.
Hruby, Victor J.
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2012, 44 (03) : 222 - 255
[25] Study of a Novel Asymmetric Synthesis of α-Amino Acids
Hu Ai-Guo
Wang Shan-Wei
Zhao Xue-Mei
Wang Ji-Tao
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2001, 22 : 124 - 129
[26] Protonation-Assisted Conjugate Addition of Axially Chiral Enolates: Asymmetric Synthesis of Multisubstituted β-Lactams from α-Amino Acids
Yoshimura, Tomoyuki
Takuwa, Masatoshi
Tomohara, Keisuke
Uyama, Makoto
Hayashi, Kazuhiro
Yang, Pan
Hyakutake, Ryuichi
Sasamori, Takahiro
Tokitoh, Norihiro
Kawabata, Takeo
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (48) : 15330 - 15336
[27] Asymmetric synthesis of aliphatic α-amino and γ-hydroxy α-amino acids and introduction of a template for crystallization-induced asymmetric transformation
Jakubec, Pavol
Berkes, Dusan
Kolarovic, Andrej
Povazanec, Frantisek
SYNTHESIS-STUTTGART, 2006, (23): : 4032 - 4040
[28] Asymmetric Synthesis of β-Amino Phosphonate Derivatives through Natural Amino Acids Derived α-Diazophosphonates
Hu, Chenfei
Cai, Yan
Abudukeremu, Munira
Miao, Zhiwei
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (10) : 2135 - 2141
[29] Expanding the Application Range of Aldolases: Novel Asymmetric Syntheses of α-Methylated β-Hydroxy α-Amino Acids and β-Amino Alcohols
Baer, Katrin
Dueckers, Nina
Hummel, Werner
Groeger, Harald
CHEMCATCHEM, 2010, 2 (08) : 939 - 942
[30] Asymmetric α-Fluoroalkyl-α-Amino Acids: Recent Advances in Their Synthesis and Applications
Picois, Nathan
Boutahri, Yazid
Milbeo, Pierre
Zanato, Chiara
Lensen, Nathalie
Chaume, Gregory
Brigaud, Thierry
MOLECULES, 2024, 29 (06):

← 1 2 3 4 5 →