- The intramolecular Diels-Alder vinylfuran (IMDAV) reaction: a short approach to aza-analogues of pinguisane-type sesquiterpenes
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Abstract The reaction of readily accessible (3-furyl)allylamines with maleic anhydride, followed by a domino sequence involving acylation/cycloaddition/proton shift steps, led to the formation of furo[2,3-f]isoindoles - the aza-analogs of pinguisane-type
- Horak, Yuriy I.,Lytvyn, Roman Z.,Homza, Yuriy V.,Zaytsev, Vladimir P.,Mertsalov, Dmitriy F.,Babkina, Maria N.,Nikitina, Eugenia V.,Lis, Tadeusz,Kinzhybalo, Vasyl,Matiychuk, Vasyl S.,Zubkov, Fedor I.,Varlamov, Alexey V.,Obushak, Mykola D.
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- Development of Chiral Spiro Phosphoramidites for Rhodium-Catalyzed Enantioselective Reactions
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A series of 1,1′-spirobiindane-7,7′-diol (SPINOL) analogues bearing a 2,2′-dimethyl-, cyclopentyl-, or cyclohexyl-fused ring were synthesized, and their distinct structural features were elucidated by X-ray crystallography. On the basis of these scaffolds, chiral monophosphoramidite ligands 6 a–m were synthesized, which demonstrated excellent enantioselectivity in RhI-catalyzed asymmetric hydrogenation of a dehydro amino acid methyl ester. Ligands 6 a–m were also successfully applied in the RhI-catalyzed enantioselective [4+2] cycloaddition of α,β-unsaturated imines with isocyanates, which afforded the corresponding pyrimidinones in good yields (60–92 %) with high enantioselectivities (75–92 % ee).
- Zheng, Zhiyao,Cao, Yuxi,Zhu, Dongsheng,Wang, Zheng,Ding, Kuiling
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supporting information
p. 9491 - 9497
(2019/04/08)
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- Easy construction of furo[2,3-f]isoindole core by the IMDAV reaction between 3-(furyl)allylamines and α,β-unsaturated acid anhydrides
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The vinylogues of furfurylamines, easily available in two steps from furylacroleins (3-(furyl)allylamines), were studied in a tandem N-acylation/intramolecular [4+2] cycloaddition with maleic, pyrocinchonic, and citraconic anhydrides, as well as furylacry
- Zubkov, Fedor I.,Zaytsev, Vladimir P.,Mertsalov, Dmitriy F.,Nikitina, Eugenia V.,Horak, Yuriy I.,Lytvyn, Roman Z.,Homza, Yuriy V.,Obushak, Mykola D.,Dorovatovskii, Pavel V.,Khrustalev, Victor N.,Varlamov, Alexey V.
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p. 2239 - 2253
(2016/04/19)
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- N-heterocyclic carbene and Bronsted acid cooperative catalysis: Asymmetric synthesis of trans -γ-Lactams
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An efficient enantioselective approach to form trans-γ-lactams in up to 99% yield, 93% ee, and >20/1 dr using unactivated imines has been developed. The cyclohexyl-substituted azolium and the weak base sodium o-chlorobenzoate are most suitable for this tr
- Zhao, Xiaodan,Dirocco, Daniel A.,Rovis, Tomislav
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supporting information; experimental part
p. 12466 - 12469
(2011/09/16)
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- Synthesis of Schiff's bases from furylacroleins and aminopyridines in the presence of molecular sieves
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We have studied the reactions of (hetero)aromatic aldehydes with 2-aminopyridines. The results obtained suggest that molecular sieves play a role in these processes not only as a dehydrating agent but also as an acid catalyst. We have synthesized a series of novel heterocyclic azomethines.
- Iovel,Golomba,Popelis,Gaukhman,Lukevics
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p. 264 - 274
(2007/10/03)
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- Propane phosphonic acid anhydride: A mild reagent for β-lactam synthesis
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The use of propane phosphonic acid anhydride (T3P()) as an acid activating reagent was demonstrated in the syntheses of cis β-lactams from the reactions of a glycine Dane salt and various imines.
- Crichfield,Hart,Lampert,Vaid
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p. 3737 - 3744
(2007/10/03)
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