Recent Developments in Catalytic Asymmetric Inverse-Electron-Demand Diels-Alder Reaction

被引:477
作者
Jiang, Xianxing [1 ]
Wang, Rui [1 ]
机构
[1] Lanzhou Univ, Sch Basic Med Sci, Inst Biochem & Mol Biol, Key Lab Preclin Study New Drugs Gansu Prov, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
CHIRAL PHOSPHORIC-ACID; HIGHLY ENANTIOSELECTIVE SYNTHESIS; BETA; GAMMA-UNSATURATED ALPHA-KETOESTERS; BIFUNCTIONAL ORGANOCATALYTIC STRATEGY; A-RING PRECURSOR; LEWIS-ACID; BETA-MANNOPYRANOSIDES; TRANSITION-METAL; CONCISE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS;
D O I
10.1021/cr300436a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Researchers discuss the latest developments in catalytic asymmetric inverse-electron-demand Diels-Alder (DA reaction. The catalytic asymmetric inverse-electron-demand Diels-Alder (IEDDA) reaction has emerged as a powerful and atom-economical tool for the stereoselective construction of functionalized six-membered rings with control of regio-, diastereo-, and enantioselectivity. It features mild reaction conditions, a tolerance of a diverse range of functional groups, and the easy construction of carbon-carbon and carbon-heteroatom bonds, which allows facile, stereospecific entry into the formation of functionalized ring systems. The high density of functional groups and up to four stereocenters of the resulting products renders them exceptionally versatile synthetic intermediates. Researchers discuss the latest efforts and advances in asymmetric IEDDA reaction through catalytic methodologies including the Lewis acidic metal complexes or organic molecules-catalyzed asymmetric IEDDA reaction through the LUMO-lowering strategy.
引用
收藏
页码:5515 / 5546
页数:32
相关论文
共 302 条
[91]  
2-K
[92]   C2-symmetric copper(II) complexes as chiral Lewis acids.: Scope and mechanism of catalytic enantioselective aldol additions of enolsilanes to (benzyloxy)acetaldehyde [J].
Evans, DA ;
Kozlowski, MC ;
Murry, JA ;
Burgey, CS ;
Campos, KR ;
Connell, BT ;
Staples, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) :669-685
[93]   Cationic bis(oxazoline) and pyridyl-bis(oxazoline)Cu(II) and Zn(II) Lewis acid catalysts. A comparative study in catalysis of Diels-Alder and aldol reactions [J].
Evans, DA ;
Kozlowski, MC ;
Tedrow, JS .
TETRAHEDRON LETTERS, 1996, 37 (42) :7481-7484
[94]   Catalytic enantioselective hetero Diels-Alder reactions of α,β-unsaturated acyl phosphonates with enol ethers [J].
Evans, DA ;
Johnson, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (19) :4895-4896
[95]   Reversal in enantioselectivity of tert-butyl versus phenyl-substituted bis(oxazoline)copper(II) catalyzed hetero Diels-Alder and ene reactions.: Crystallographic and mechanistic studies [J].
Evans, DA ;
Johnson, JS ;
Burgey, CS ;
Campos, KR .
TETRAHEDRON LETTERS, 1999, 40 (15) :2879-2882
[96]   3 NEW BIOACTIVE STYRYLLACTONES FROM GONIOTHALAMUS-GIGANTEUS (ANNONACEAE) [J].
FANG, XP ;
ANDERSON, JE ;
CHANG, CJ ;
MCLAUGHLIN, JL .
TETRAHEDRON, 1991, 47 (47) :9751-9758
[97]   Stereoselective Synthesis of (+)-Goniodiol, (+)-Goniotriol, (-)-Goniofupyrone, and (+)-Altholactone Using a Catalytic Asymmetric Hetero-Diels-Alder/Allylboration Approach [J].
Favre, Annaick ;
Carreaux, Francois ;
Deligny, Michael ;
Carboni, Bertrand .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (29) :4900-4907
[98]   Sanglifehrins A, B, C and D, novel cyclophilin-binding compounds isolated from Streptomyces sp A92-308110 -: II.: Structure elucidation, stereochemistry and physico-chemical properties [J].
Fehr, T ;
Kallen, J ;
Oberer, L ;
Sanglier, JJ ;
Schilling, W .
JOURNAL OF ANTIBIOTICS, 1999, 52 (05) :474-479
[99]   Highly diastereoselective synthesis of new indolopyrroloquinolines through intramolecular itnino Diels-Alder reactions [J].
Gaddam, Vikram ;
Nagarajan, Rajagopal .
TETRAHEDRON LETTERS, 2007, 48 (41) :7335-7338
[100]  
Gademann K, 2002, ANGEW CHEM INT EDIT, V41, P3059, DOI 10.1002/1521-3773(20020816)41:16<3059::AID-ANIE3059>3.0.CO