Chiral metal phosphate catalysis: highly asymmetric hetero-Diels–Alder reactions

2014 ◽  
Vol 50 (91) ◽  
pp. 14187-14190 ◽  
Author(s):  
Tao Liang ◽  
Guilong Li ◽  
Lukasz Wojtas ◽  
Jon C. Antilla
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Metal Phosphate ◽  
X Ray ◽  
Keto Esters ◽  
Diels Alder Reaction

A highly enantioselective hetero-Diels–Alder reaction of α-keto esters and isatins catalyzed by chiral calcium BINOL-derived phosphates (X-ray) is reported.

Stereo-controlled synthesis of polyheterocycles via the diene-transmissive hetero-Diels–Alder reaction of β,γ-unsaturated α-keto esters

2015 ◽  
Vol 13 (21) ◽  
pp. 5875-5879 ◽  
Author(s):  
Takashi Otani ◽  
Yumiko Tamai ◽  
Kazunori Seki ◽  
Tomohiro Kikuchi ◽  
Taiichiro Miyazawa ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Controlled Synthesis ◽  
Keto Esters ◽  
Diels Alder Reaction ◽  
Stereocontrolled Synthesis

Stereocontrolled synthesis of polyheterocycles via the diene-transmissive hetero Diels–Alder reaction of β,χ-unsaturated α-keto esters is described.

scholarly journals Two-Carbon Ring Enlargement of Five-, Six-, and Seven-Membered 1-Aza-2-vinylcycloalk-2-enes with Dimethyl Acetylenedicarboxylate and Subsequent Thermal Isomerization Reactions

2006 ◽  
Vol 61 (4) ◽  
pp. 385-395 ◽  
Author(s):  
Gerhard Maas ◽  
Robert Reinhard ◽  
Hans-Georg Herz
Keyword(s):  
Elevated Temperatures ◽  
Alder Reaction ◽  
Thermal Isomerization ◽  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
X Ray ◽  
Ring Enlargement ◽  
Diels Alder Reaction ◽  
Carbon Ring ◽  
Electrocyclic Reaction

2-Aminodienes, in which the enamine function is incorporated in a five-, six-, or seven-membered ring, react with dimethyl acetylenedicarboxylate in a sequence of [2+2] cycloaddition and electrocyclic ring-opening to form the two-carbon ring expanded unsaturated heterocycles, i.e., 3,4- dicarboxylate substituted 6,7-dihydro-1H-azepines 3, 8 and 21, 1,6,7,8-tetrahydroazocines 22, and 6,7,8,9-tetrahydro-1H-azonines 13. Similarly, 2-[(2-thienyl)ethynyl]-4,5,6,7-tetrahydro-1H-azepine 9 is converted into 2-[(2-thienyl)ethynyl]-6,7,8,9-1H-azonine-3,4-dicarboxylate 10 which was characterized by X-ray structure determination. The eight- and nine-membered azaheterocycles 22 and 13, which have not been isolated, undergo thermal isomerization at elevated temperatures. Thus, ring contraction by a 6π-electrocyclic reaction takes place for N-methyl substituted azonine 13, while the N-allyl moiety of azocines 22 engages in an intramolecular Diels-Alder reaction or a 1,7- electrocyclization reaction

Direct construction of chiral quaternary dihydropyranones through highly enantioselective organocatalytic hetero-Diels–Alder reactions of olefinic azlactones

2016 ◽  
Vol 3 (5) ◽  
pp. 598-602 ◽  
Author(s):  
Tai-Ping Gao ◽  
Dan Liu ◽  
Jun-Bing Lin ◽  
Xiu-Qin Hu ◽  
Zhu-Yin Wang ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Direct Construction ◽  
Keto Esters ◽  
Diels Alder Reaction

The first organocatalytic hetero-Diels–Alder reaction of an in situ generated diene with α-keto esters was reported for the construction of chiral dihydropyranones.

ChemInform Abstract: Abnormal Diels-Alder Reaction of 5-Alkoxyoxazoles with Tetracyanoethylene and X-Ray Crystal Structure of an Adduct.

ChemInform ◽  
2010 ◽  
Vol 23 (44) ◽  
pp. no-no
Author(s):  
T. IBATA ◽  
Y. ISOGAMI ◽  
H. NAKAWA ◽  
H. TAMURA ◽  
H. SUGA ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Alder Reaction ◽  
Diels Alder ◽  
X Ray ◽  
Diels Alder Reaction

Molecular Topology of Linked Anthracenes: X-Ray Structure Analyses of Alkyl Di-9-anthryl-glycolates, 9-Anthryl 9-Anthrylmethyl Ethers and Their Photoisomers

1989 ◽  
Vol 42 (11) ◽  
pp. 1869 ◽  
Author(s):  
HD Becker ◽  
BW Skelton ◽  
AH White
Keyword(s):  
Single Crystal ◽  
Alder Reaction ◽  
Diels Alder ◽  
Molecular Structures ◽  
Molecular Topology ◽  
X Ray Diffraction ◽  
X Ray ◽  
Diels Alder Reaction ◽  
Photochemical Isomerization ◽  
Spatial Demand

The molecular structures of ethyl di-9-anthrylglycolate (1) and methyl di-9-anthrylglycolate (2), as well as those of three isomerization products of (2), have been established by single-crystal X-ray diffraction studies. In both (1) and (2), the anthracenemoieties are characterized by marked deviations from planarity. The stereospecific course of the thermal and photochemical isomerization of (2) by Diels -Alder reaction is suggested to be governed by the spatial demand of the alkoxycarbonyl group. Base-catalysed isomerization of (2) by migration of 9-anthryl from carbon to oxygen is associated with steric relief.

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