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1.
Junyan Ma Danfeng Huang Ke‐Hu Wang Yanli Xu Siying Chong Yingpeng Su Ying Fu Yulai Hu 《应用有机金属化学》2016,30(7):571-576
An efficient process for the synthesis of homoallylic amines and N′‐homoallylic hydrazides is developed from the one‐pot reaction of carbonyl compounds, amines or N‐acylhydrazines, allyllic bromide and tin powder using water as solvent. N‐Acylhydrazines are found to be more reactive than amines in these processes. They can react not only with aldehydes but also with ketones to give the corresponding N′‐homoallylic hydrazides. Copyright © 2016 John Wiley & Sons, Ltd. 相似文献
2.
Enantioselective Generation of Adjacent Stereocenters in a Copper‐Catalyzed Three‐Component Coupling of Imines,Allenes, and Diboranes
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Kay Yeung Rebecca E. Ruscoe Dr. James Rae Dr. Alexander P. Pulis Prof. Dr. David J. Procter 《Angewandte Chemie (International ed. in English)》2016,55(39):11912-11916
A highly enantio‐ and diastereoselective copper‐catalyzed three‐component coupling affords the first general synthesis of homoallylic amines bearing adjacent stereocenters from achiral starting materials. The method utilizes a commercially available NHC ligand and copper source, operates at ambient temperature, couples readily available simple imines, allenes, and diboranes, and yields high‐value homoallylic amines that exhibit versatile amino, alkenyl, and boryl units. 相似文献
3.
Kay Yeung Rebecca E. Ruscoe James Rae Alexander P. Pulis David J. Procter 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2016,128(39):12091-12095
A highly enantio‐ and diastereoselective copper‐catalyzed three‐component coupling affords the first general synthesis of homoallylic amines bearing adjacent stereocenters from achiral starting materials. The method utilizes a commercially available NHC ligand and copper source, operates at ambient temperature, couples readily available simple imines, allenes, and diboranes, and yields high‐value homoallylic amines that exhibit versatile amino, alkenyl, and boryl units. 相似文献
4.
Colin M. Pearson James W. B. Fyfe Thomas N. Snaddon 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2019,131(31):10631-10637
Herein, we report a modular synthetic route to linear and branched homoallylic amines that operates through a sequential one‐pot Lewis base/transition‐metal catalyzed allylic alkylation/Hofmann rearrangement strategy. This protocol is operationally trivial, proceeds from simple and easily prepared substrates and catalysts, and enables all aspects of regio‐ and stereoselectivity to be controlled through a conserved experimental protocol. Overall, the high levels of enantio‐, regio‐, and diastereoselectivity obtained, in concert with the ability to access orthogonally protected or free amines, render this a straightforward and effective approach for the preparation of useful enantioenriched homoallylic amines. We have also demonstrated the utility of the products in the context of pharmaceutical synthesis. 相似文献
5.
Iron trichloride hexahydrate has proved to be a very effective catalyst for the three‐component condensation of aromatic aldehydes, amines and allyltributylstannane, which produces high yields of homoallylic amines in water in the presence of surfactant SDS. Copyright © 2009 John Wiley & Sons, Ltd. 相似文献
6.
Highly Diastereo‐ and Enantioselective Cu‐Catalyzed Borylative Coupling of 1,3‐Dienes and Aldimines
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Liyin Jiang Prof. Dr. Peng Cao Dr. Min Wang Bin Chen Bing Wang Prof. Dr. Jian Liao 《Angewandte Chemie (International ed. in English)》2016,55(44):13854-13858
A Cu‐catalyzed diastereo‐ and enantioselective borylative coupling reaction of 1,3‐dienes with imines was realized. Branched homoallylic amines are readily prepared in a syn‐selective manner with high regio‐, diastereo‐ and enantioselectivity. Moreover, these three‐component coupling reactions feature good functional‐group compatibility and easy access to the substrates and catalyst. 相似文献
7.
Biswanath Das Bommena Ravikanth Kongara Ravinder Reddy Bommena Vittal Rao 《Helvetica chimica acta》2007,90(1):105-109
Zirconyl chloride (ZrOCl2) catalyzes efficiently the one‐pot three component reactions of aldehydes, amines, and allyltributylstannane at room temperature to furnish the corresponding homoallylic amines in short reaction times and in excellent yields. 相似文献
8.
Diastereoselective allylation of imine derived from N‐glyoxyloyl camphorpyrazolidinone and amines was treated with allyltributylstannane in the presence of triflic acid. The corresponding optically enriched homoallylic amines were obtained in reasonable to high material yields and with practical levels of stereoselectivity in 10 min at ambient temperature. 相似文献
9.
以磷钼酸作为催化剂,芳香醛、胺和三丁基烯丙基锡三组分在水作为溶剂,室温下高产率的得到相应的烯丙基胺。 相似文献
10.
Sabrina Ouizem Dr. Sandrine Cheramy Dr. Candice Botuha Prof. Fabrice Chemla Dr. Franck Ferreira Dr. Alejandro Pérez‐Luna 《Chemistry (Weinheim an der Bergstrasse, Germany)》2010,16(42):12668-12677
Stereoselective cyclization of zincated α‐N‐homoallylamino nitriles has been developed. Following treatment with lithium diisopropylamide (LDA) and transmetalation with zinc bromide, α‐N‐(1‐phenylethyl)‐N‐homoallylamino nitriles lead to 2,3‐methanopyrrolidines in moderate to good yields (up to 66 %) and excellent selectivities (up to >98:2). With substrates derived from α‐branched homoallylic amines, a stereospecific inversion of the homoallylic stereogenic center was observed. To account for this, a mechanistic rationale involving the formation of zincioiminium ions from zincated α‐amino nitriles is put forward. 2,3‐Methanopyrrolidines should then arise from a sequence involving an aza‐Cope rearrangement providing a configurationally stable (2‐azoniaallyl)zinc species that then undergoes a [3+2] cycloaddition reaction. 相似文献
11.
Diana C. Fager Ryan J. Morrison Amir H. Hoveyda 《Angewandte Chemie (International ed. in English)》2020,59(28):11448-11455
A method for catalytic regio‐ and enantioselective synthesis of trifluoromethyl‐substituted and aryl‐, heteroaryl‐, alkenyl‐, and alkynyl‐substituted homoallylic α‐tertiary NH2‐amines is introduced. Easy‐to‐synthesize and robust N‐silyl ketimines are converted to NH‐ketimines in situ, which then react with a Z‐allyl boronate. Transformations are promoted by a readily accessible l ‐threonine‐derived aminophenol‐based boryl catalyst, affording the desired products in up to 91 % yield, >98:2 α:γ selectivity, >98:2 Z:E selectivity, and >99:1 enantiomeric ratio. A commercially available aminophenol may be used, and allyl boronates, which may contain an alkyl‐, a chloro‐, or a bromo‐substituted Z‐alkene, can either be purchased or prepared by catalytic stereoretentive cross‐metathesis. What is more, Z‐trisubstituted allyl boronates may be used. Various chemo‐, regio‐, and diastereoselective transformations of the α‐tertiary homoallylic NH2‐amine products highlight the utility of the approach; this includes diastereo‐ and regioselective epoxide formation/trichloroacetic acid cleavage to generate differentiated diol derivatives. 相似文献
12.
Base‐Catalyzed Intramolecular Hydroamination of Cyclohexa‐2,5‐dienes: Insights into the Mechanism through DFT Calculations and Application to the Total Synthesis of epi‐Elwesine
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Dr. Géraldine Rousseau Dr. Raphaël Lebeuf Dr. Kurt Schenk Dr. Frédéric Castet Dr. Frédéric Robert Prof. Dr. Yannick Landais 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(45):14771-14782
The base‐catalyzed intramolecular hydroamination of 1‐ethylaminocyclohexa‐2,5‐dienes is described. The transformation proceeds through isomerization of the cyclohexa‐1,4‐dienyl fragment into the corresponding conjugated 1,3‐diene prior to the hydroamination step. Attaching a chiral glycinol ether auxiliary on the amino group allows the protonation to occur with complete diastereocontrol. The resulting lithium amide then adds onto the 1,3‐dienyl moiety, affording the desired fused pyrrolidine ring along with the corresponding lithium allylic anion. Protonation of the latter then proceeds with high regiocontrol to favor the resulting allylic amines. In contrast, when the reaction was performed on primary amines, fused pyrrolidines bearing a homoallylic amino group were obtained. The stereochemical course of the process and determination of the reaction pathways were established based on calculations performed at the DFT level. Finally, application of the methodology to the enantioselective synthesis of (+)‐epi‐elwesine, a crinane alkaloid, is described. 相似文献
13.
Summaryof main observation and conclusion Herein,we developed an Ir/phase-transfer-catalysiscooperatively catalyzed asymmetric cascade allyla-tion/2-aza-Cope rearrangement of aldimine esters to prepare synthetically important homoallylic amines in good yields with excellent enantioselectivi-ties.Compared with the bimetallic catalytic system to realize this transformation,the current cooperative Ir/tetrabutyl ammonium bromide catalytic system provides an alternative but more practical approach,which not only simplify the manipulation process but also increase the cost efficiency. 相似文献
14.
Dual Catalytic Decarboxylative Allylations of α‐Amino Acids and Their Divergent Mechanisms
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Simon B. Lang Kathryn M. O'Nele Dr. Justin T. Douglas Prof. Dr. Jon A. Tunge 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(51):18589-18593
The room temperature radical decarboxylative allylation of N‐protected α‐amino acids and esters has been accomplished via a combination of palladium and photoredox catalysis to provide homoallylic amines. Mechanistic investigations revealed that the stability of the α‐amino radical, which is formed by decarboxylation, dictates the predominant reaction pathway between competing mechanisms. 相似文献
15.
An efficient method for the asymmetric synthesis of C-aliphatic homoallylic amines with up to 94% yield and 80% de is reported. Ring-closing metathesis of several chiral homoallylic amines using the second-generation Grubbs catalyst provided easy access to a wide variety of cyclohexenylamines. 相似文献
16.
《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2017,129(33):10076-10080
Asymmetric nitrene‐transfer reactions are a powerful tool for the preparation of enantioenriched amine building blocks. Reported herein are chemo‐ and enantioselective silver‐catalyzed aminations which transform di‐ and trisubstituted homoallylic carbamates into [4.1.0]‐carbamate‐tethered aziridines in good yields and with ee values of up to 92 %. The effects of the substrate, silver counteranion, ligand, solvent, and temperature on both the chemoselectivity and ee value were explored. Stereochemical models were proposed to rationalize the observed absolute stereochemistry of the aziridines, which undergo nucleophilic ring opening to yield enantioenriched amines with no erosion in stereochemical integrity. 相似文献
17.
A highly diastereoselective addition of substituted racemic allylic zinc reagents to chiral N- tert-butanesulfinylimines resulting in the formation of homoallylic amines is reported. This method is quite general and also efficient for the preparation of enantiomerically pure homoallylic amines bearing quaternary centers and also adjacent quaternary centers. 相似文献
18.
Copper‐Catalyzed Borylative Cross‐Coupling of Allenes and Imines: Selective Three‐Component Assembly of Branched Homoallyl Amines
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Dr. James Rae Kay Yeung Dr. Joseph J. W. McDouall Prof. Dr. David J. Procter 《Angewandte Chemie (International ed. in English)》2016,55(3):1102-1107
A copper‐catalyzed three‐component coupling of allenes, bis(pinacolato)diboron, and imines allows regio‐, chemo‐, and diastereoselective assembly of branched α,β‐substituted‐γ‐boryl homoallylic amines, that is, products bearing versatile amino, alkenyl, and borane functionality. Alternatively, convenient oxidative workup allows access to α‐substituted‐β‐amino ketones. A computational study has been used to probe the stereochemical course of the cross‐coupling. 相似文献
19.
Pabitra Kumar Kalita Susanta Kumar Borthakur Runumi Das Chandan Jyoti Choudhury 《合成通讯》2013,43(21):2444-2453
This paper describes a general method for the synthesis of homoallylic alcohols and amines by nucleophilic addition reaction of allyltributylstannane to carbonyl compounds and aldimines where iodine acts as a catalyst in H2O/acetic acid (1:1) medium. Only 10 mol% of I2 is required for various organic transformations. By using this process, various homoallylic alcohols and amines are produced in good to excellent yields. 相似文献
20.
[reaction: see text] An efficient method for the highly diastereoselective synthesis of chiral homoallylic amines by Zn-mediated allylation of chiral N-tert-butanesulfinyl imines at room temperature was developed. By simply tuning the reaction conditions, the method allows the achievement of a highly remarkable opposite stereocontrol, affording the desired stereochemical outcome in good yield and with excellent diastereoselectivity (up to 98% dr). With N-sulfinyl ketimines, the corresponding quaternary carbon-containing chiral homoallylic amines could also be produced. 相似文献