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1.
Organocatalytic,Enantioselective Synthesis of Cyclohexadienone Containing Hindered Spirocyclic Ethers through an Oxidative Dearomatization/Oxa‐Michael Addition Sequence
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Reddy Rajasekhar Reddy Dr. Satish Sonbarao Gudup Prof. Prasanta Ghorai 《Angewandte Chemie (International ed. in English)》2016,55(48):15115-15119
An unprecedented enantioselective oxa‐Michael reaction of α‐tertiary alcohols using cinchona‐alkaloid‐based chiral bifunctional squaramide catalysts is reported. An oxidative dearomatization of phenol followed by an enantioselective oxa‐Michael addition sequence provided a broad array of chiral sterically hindered tetrahydrofurans and tetrahydropyrans attached to a cyclohexadienone moiety in spiro fashion. In general, good yields and excellent enantioselectivities (up to 99 %) were observed. The chiral oxo‐cycles obtained have easily been transformed into chromans without disturbing the enantioselectivity. 相似文献
2.
Organocatalytic Enantioselective Synthesis of 1,4‐Dioxanes and Other Oxa‐Heterocycles by Oxetane Desymmetrization
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A new asymmetric synthesis of chiral 1,4‐dioxanes and other oxa‐heterocycles has been developed by means of organocatalytic enantioselective desymmetrization of oxetanes. This mild process proceeds with exceedingly high efficiency and enantioselectivity to establish the quaternary stereocenters. This method complements the existing, yet limited, strategies for the synthesis of these oxa‐heterocycles. 相似文献
3.
Organocatalytic Cascade Reactions: Towards the Diversification of Hydroisochromenes and Chromenes through Two Different Activation Modes
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Dr. David Cruz Cruz Rasmus Mose Dr. Clarisa Villegas Gómez Stine V. Torbensen Martin S. Larsen Prof. Dr. Karl Anker Jørgensen 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(36):11331-11335
The organocatalytic enantioselective syntheses of functionalized hydroisochromenes and chromenes by trienamine‐mediated [4+2]‐cycloaddition/nucleophilic ring‐closing and iminium‐ion/aminal‐mediated oxa‐Michael/Michael/nucleophilic ring‐closing with 2‐nitroallylic alcohols are presented. The corresponding cycloadducts, with up to five stereocenters, are formed in good yield and excellent enantioselectivities. The synthetic applications of the obtained products have been demonstrated. 相似文献
4.
Organocatalyzed Cascade Aza‐Michael/Michael Addition for the Asymmetric Construction of Highly Functionalized Spiropyrazolone Tetrahydroquinolines
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An organocatalyzed diastereo‐ and enantioselective cascade aza‐Michael/Michael addition of 2‐tosylaminoenones to unsaturated pyrazolones has been developed to afford novel chiral spiropyrazolone tetrahydroquinolines containing three contiguous stereocenters. This cascade reaction proceeded well with 2 mol % chiral bifunctional tertiary amine squaramide catalyst to give the desired products in excellent yields (up to 99 %) with excellent diastereoselectivity (up to >25:1 diastereomeric ratio) and high enantioselectivity (up to 91 % enantiomeric excess). 相似文献
5.
Cinchonamine Squaramide Catalyzed Asymmetric aza‐Michael Reaction: Dihydroisoquinolines and Tetrahydropyridines
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Tarun Kumar Roy Biswajit Parhi Dr. Prasanta Ghorai 《Angewandte Chemie (International ed. in English)》2018,57(30):9397-9401
The first example of a chiral cinchona‐squaramide catalyzed enantioselective intramolecular aza‐Michael addition for the synthesis of dihydroisoquinolines and tetrahydropyridines has been developed. In general, good yields and excellent enantioselctivities were observed. Broad classes of Michael acceptors, such as enones, esters, thioesters, and Weinreb amides, were successful substrates. The possibility of recycling the catalysts has also been demonstrated. An oxidation of combined enamine and keto functionalities on chiral dihydroisoquinolines leads to a single diastereomer of an architecturally unprecedented tetracyclic core without loss in enantioselectivity. 相似文献
6.
An efficient enantioselective cascade sulfa‐Michael/Michael addition reaction of trans‐3‐(2‐mercaptophenyl)‐2‐propenoic acid ethyl ester with nitroalkenes catalyzed by a chiral squaramide catalyst was disclosed. This cascade reaction afforded thiochroman derivatives with three contiguous stereocenters in high yields (up to 94%), excellent diastereoselectivities (up to >25:1 dr) and enantioselectivities (up to 99% ee). 相似文献
7.
Yi‐Feng Wang Wei Zhang Shu‐Ping Luo Dr. Bai‐Lin Li Ai‐Bao Xia Ai‐Guo Zhong Dr. Dan‐Qian Xu Dr. 《化学:亚洲杂志》2009,4(12):1834-1838
Generally, amine‐catalyzed enantioselective transformations rely on chiral enamine or unsaturated iminium intermediates. Herein, we report a protocol involving dual activation by an aromatic iminium and hydrogen‐bonding. An enantioselective aza‐Michael–Henry domino reaction of 2‐aminobenzaldehydes with nitroolefins has been developed through this protocol using primary amine thiourea catalysts to provide a variety of 3‐nitro‐1,2‐dihydroquinolines in moderate yields and with up to 90 % ee. The mechanism for the catalytic enantioselective reaction was confirmed by ESI mass spectrometric detection of the reaction intermediates. The products formed are substructures found in skeletons of important biological and pharmaceutical molecules. 相似文献
8.
Basi V. Subba Reddy Lavudia Srinivas Pathuri Sivaramakrishna Reddy Bhemavarapu Phaneendra Reddy Attaluri R. Prasad Jhillu S. Yadav 《Helvetica chimica acta》2014,97(10):1326-1332
A stereoselective total synthesis of phomonol, following organocatalytic enantioselective epoxidation and intramolecular oxa‐Michael reaction as key steps, is described. The use of readily available D ‐tartaric acid as a chiral source renders this approach quite simple and attractive. 相似文献
9.
Chi He Chenlong Zhu Bingnan Wang Prof. Dr. Hanfeng Ding 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(46):15053-15060
In this study, a concise and stereoselective approach for the divergent total synthesis of (?)‐indoxamycins A–F is described. The key steps of the strategy include an Ireland–Claisen rearrangement, an enantioselective 1,6‐enyne reductive cyclization, and a tandem 1,2‐addition/oxa‐Michael/methylenation reaction. The relative and absolute configuration of these natural products has been unambiguously elucidated, and their cytotoxic activities against HT‐29 and A‐549 tumor cell lines are also reported. 相似文献
10.
Nakajima M Yamaguchi Y Hashimoto S 《Chemical communications (Cambridge, England)》2001,(17):1596-1597
An enantioselective Michael addition of beta-keto esters to methyl vinyl ketone exploiting a chiral N,N'-dioxide-scandium trifluoromethanesulfonate complex as a catalyst affords the corresponding Michael adducts in high yields and with enantioselectivities of up to 80% ee. 相似文献
11.
Highly Enantioselective Aza‐Michael Reaction between Alkyl Amines and β‐Trifluoromethyl β‐Aryl Nitroolefins
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Prof. Dr. Yong Huang 《Angewandte Chemie (International ed. in English)》2015,54(51):15414-15418
The aza‐Michael addition reaction is a vital transformation for the synthesis of functionalized chiral amines. Despite intensive research, enantioselective aza‐Michael reactions with alkyl amines as the nitrogen donor have not been successful. We report the use of chiral N‐heterocyclic carbenes (NHCs) as noncovalent organocatalysts to promote a highly selective aza‐Michael reaction between primary alkyl amines and β‐trifluoromethyl β‐aryl nitroolefins. In contrast to classical conjugate‐addition reactions, a strategy of HOMO‐raising activation was used. Chiral trifluoromethylated amines were synthesized in high yield (up to 99 %) with excellent enantioselectivity (up to 98 % ee). 相似文献
12.
Thummalapally Srikanth Reddy Dorigondla Kumar Reddy Manchala Narasimhulu Dasari Ramesh Yenamandra Venkateswarlu 《Helvetica chimica acta》2010,93(11):2158-2163
Total synthesis of mevinic acid analog 1 has been achieved efficiently starting from chiral 2,3‐O‐isopropylidene‐D ‐glyceraldehyde ( 2 ). The synthesis involves Mitsunobu reaction and Evans' intramolecular oxa‐Michael syn‐addition reactions as key steps. 相似文献
13.
Arun Suneja Henning Jakob Loui Christoph Schneider 《Angewandte Chemie (International ed. in English)》2020,59(14):5536-5540
We describe herein a highly diastereo‐ and enantioselective [4+3]‐cycloannulation of ortho‐quinone methides and carbonyl ylides to furnish functionalized oxa‐bridged dibenzooxacines with excellent yields and stereoselectivity in a single synthetic step. The combination of rhodium and chiral phosphoric acid catalysis working in concert to generate both transient intermediates in situ provides direct access to complex bicyclic products with two quaternary and one tertiary stereogenic centers. The products may be further functionalized into valuable and enantiomerically highly enriched building blocks. 相似文献
14.
An enantioselective Michael addition of malonates to 2-enoylpyridine N-oxides catalyzed by a chiral bisoxazoline-Zn(II) complex has been developed. The corresponding Michael adducts have been obtained in high yields with up to 96% ee. A plausible transition-state model has been proposed to explain the stereochemical outcome of the reaction. 相似文献
15.
《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2017,129(30):8789-8792
A Michael addition initiated cyclopropanation/retro‐Claisen rearrangement tandem reaction was developed for the enantioselective synthesis of highly functionalized 2,5‐dihydrooxepines. In the presence of a chiral oxazaborolidinium ion (COBI) catalyst, the reaction proceeds to give good yields and high enantioselectivity. 相似文献
16.
17.
Hao Li 《Tetrahedron letters》2006,47(18):3145-3148
An enantioselective, organocatalytic Michael addition reaction of thioacetic acid with enones has been developed. The process, catalyzed by a chiral bifunctional amine thiourea, furnishes products in excellent yields with up to 63% ee. 相似文献
18.
Liu L Wu D Li X Wang S Li H Li J Wang W 《Chemical communications (Cambridge, England)》2012,48(11):1692-1694
An enantioselective Michael addition of ketones to alkylidenemalononitriles catalyzed by chiral primary amine I with (R)-5c as a co-catalyst in good yields (>90%) and with good enantioselectivities (85-96% ee) has been developed. The strategy has also been extended to a three-component version through a domino Knoevenagel/Michael sequence with similar or better outcomes. 相似文献
19.
Combining Organocatalysis with Central‐to‐Axial Chirality Conversion: Atroposelective Hantzsch‐Type Synthesis of 4‐Arylpyridines
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Ophélie Quinonero Marion Jean Dr. Nicolas Vanthuyne Prof. Dr. Christian Roussel Dr. Damien Bonne Prof. Dr. Thierry Constantieux Prof.Dr. Cyril Bressy Dr. Xavier Bugaut Prof. Dr. Jean Rodriguez 《Angewandte Chemie (International ed. in English)》2016,55(4):1401-1405
Suitably substituted enantioenriched 4‐aryl‐1,4‐dihydro‐pyridines prepared by an organocatalytic enantioselective Michael addition were oxidized with MnO2 into axially chiral 4‐arylpyridines with central‐to‐axial chirality conversion. Moderate to complete percentages (cp) were observed, and a model for the conversion of chirality is discussed. 相似文献
20.
《Tetrahedron: Asymmetry》2014,25(4):310-317
The enantioselective tandem Michael addition reaction of dimedone and related 1,3-dicarbonyl compounds with α,β-unsaturated N-acylated succinimides catalyzed by a chiral squaramide catalyst has been investigated. This reaction provides a new approach for the synthesis of chiral enol lactones in good yields with moderate to high enantioselectivities (up to 88% ee) through the enantioselective Michael addition followed by lactonization and removal of the succinimide auxiliary. 相似文献