Synthesis of polysubstituted β-amino cyclohexane carboxylic acids via Diels-Alder reaction using Ni(II)-complex stabilized β-alanine derived dienes

被引：8

作者：

Ding, Xiao ^{[1
]}

Wang, Hengshuai ^{[1
]}

Wang, Jiang ^{[1
]}

Wang, Sinan ^{[1
]}

Lin, Daizong ^{[1
]}

Lv, Li ^{[1
]}

Zhou, Yu ^{[1
]}

Luo, Xiaomin ^{[1
]}

Jiang, Hualiang ^{[1
]}

Luis Acena, Jose ^{[2
]}

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

Liu, Hong ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China

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

[3] Univ Basque Country UPV EHU, San Sebastian, Spain

来源：

AMINO ACIDS | 2013年 / 44卷 / 02期

基金：

中国国家自然科学基金;

关键词：

Diels-Alder reaction; Nickel (II); beta-Alanine; beta-Aminocyclohexane carboxylic acids; MICHAEL ADDITION-REACTIONS; EFFICIENT ASYMMETRIC-SYNTHESIS; NUCLEOPHILIC GLYCINE EQUIVALENTS; SUBSTITUTED PYROGLUTAMIC ACIDS; VIRTUALLY COMPLETE CONTROL; CHIRAL NI(II) COMPLEX; LARGE-SCALE SYNTHESIS; ALPHA-AMINO; ALDOL REACTIONS; FACE DIASTEREOSELECTIVITY;

D O I：

10.1007/s00726-012-1404-x

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

This paper describes the design and synthesis of a new class of beta-alanine derived dienes stabilized by Ni(II)-complex. Preliminary study of their Diels-Alder cycloaddition reactions with several types of dienophiles demonstrates their significant synthetic potential for the preparation of various polyfunctional beta-aminocyclohexane carboxylic acids.

引用

页码：791 / 796

页数：6

共 15 条

[1] Synthesis of polysubstituted β-amino cyclohexane carboxylic acids via Diels–Alder reaction using Ni(II)-complex stabilized β-alanine derived dienes
Xiao Ding
Hengshuai Wang
Jiang Wang
Sinan Wang
Daizong Lin
Li Lv
Yu Zhou
Xiaomin Luo
Hualiang Jiang
José Luis Aceña
Vadim A. Soloshonok
Hong Liu
Amino Acids, 2013, 44 : 791 - 796
[2] Synthesis of fluorine-containing α-amino acids in enantiomerically pure form via homologation of Ni(II) complexes of glycine and alanine Schiff bases
Luis Acena, Jose
Sorochinsky, Alexander E.
Moriwaki, Hiroki
Sato, Tatsunori
Soloshonok, Vadim A.
JOURNAL OF FLUORINE CHEMISTRY, 2013, 155 : 21 - 38
[3] Supramolecular Phthalimide Networks Via Tandem Diels-Alder Reaction-Aromatization Using Biomass-Derived Furanic Dienes
Kim, Byounghyun
Lee, Juhyen
Bae, Han Yong
Son, Seung Uk
Song, Changsik
MACROMOLECULAR RAPID COMMUNICATIONS, 2023, 44 (04)
[4] Three-component synthesis of polysubstituted benzene derivatives via Diels-Alder reaction of cyclopentadienone acetal with alkyne
Sato, S
Isobe, H
Tanaka, T
Ushijima, T
Nakamura, E
TETRAHEDRON, 2005, 61 (48) : 11449 - 11455
[5] Diels-Alder reaction of Ni(II) β-vinyl-meso-tetraphenylporphyrin;: A general method for synthesis of functionalized porphyrins
Matsumoto, K
Kimura, S
Morishita, T
Misumi, Y
Hayashi, N
SYNLETT, 2000, (02) : 233 - 235
[6] REACTIONS OF COMPLEX LIGANDS .61. OXACYCLOALKENYLIDENE COMPLEXES OF CHROMIUM, MOLYBDENUM, AND TUNGSTEN - SYNTHESIS, THEIR ANNULATION WITH ALKYNES AND DIELS-ALDER REACTION WITH DIENES
CHRISTOFFERS, J
DOTZ, KH
CHEMISCHE BERICHTE, 1995, 128 (02) : 157 - 161
[7] Asymmetric Synthesis of Chiral Heterocyclic Amino Acids via the Alkylation of the Ni(II) Complex of Glycine and Alkyl Halides
Chen, Hui
Wang, Jiang
Zhou, Shengbin
Liu, Hong
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17) : 7872 - 7879
[8] Development of Catalytic and Enantioselective Diels-Alder Reaction of Electron-Rich Dienes Using Chiral Rare-Earth Metal Complex
Harada, Shinji
Morikawa, Takahiro
Hiraoka, Shiharu
Nishida, Atsushi
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2013, 71 (08) : 818 - 829
[9] Reaction Prediction using Density Functional Theory Calculations: A Study into the Synthesis of Safranal via Diels-Alder Reactions
Wagner, Gabriele
Vandati, Nadia
Howkins, Ashley
Cubitt, Louisa
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2011, 66 (11): : 1141 - 1150
[10] Synthesis of Novel Fluoranthene-Based Conformationally Constrained α-Amino Acid Derivatives and Polycyclic Aromatics via the Diels-Alder Reaction
Kotha, Sambasivarao
Meshram, Milind
SYNTHESIS-STUTTGART, 2014, 46 (11): : 1525 - 1531

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