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1.
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
2.
A highly practical and efficient asymmetric synthesis of chiral homoallylic amines by In-mediated allylation of chiral N-tert-butanesulfinyl imines in aqueous media at room temperature was developed. With 2-formylbenzoate imine substrates, the method allows the highly enantioselective achievement of a variety of pharmacologically important 3-allyl isoindolinone compounds. 相似文献
3.
Xiang-Chen Qiao Shou-Fei Zhu Wang-Qiao Chen Qi-Lin Zhou 《Tetrahedron: Asymmetry》2010,21(9-10):1216-1220
A palladium-catalyzed asymmetric umpolung allylation reaction of imines with allylic alcohols has been developed. In the presence of chiral spiro phosphoramidite ligand 4, the allylation was accomplished with high yields and good enantioselectivities. The use of highly stable and easily available allylic alcohols instead of allylic metal reagents facilitated the preparation of chiral homoallylic amines. 相似文献
4.
Optically pure secondary homoallylic amines, obtained by highly diastereoselective addition of allylmetal reagents to imines derived from chiral amines, were N-dealkylated, and the primary amines were converted to N-acryloyl amides. Then, ring closing metathesis gave delta-substituted delta-lactams in good overall yields. 相似文献
5.
Jian Li Wenxian Lv Danfeng Huang Ke‐Hu Wang Teng Niu Yingpeng Su Yulai Hu 《应用有机金属化学》2014,28(4):286-289
A convenient and facile method for the synthesis of homoallylic amines was disclosed. The one‐pot reaction of aldehydes, aromatic amines and allylic bromide with tin powder at room temperature could afford the homoallylic amines in good to excellent yield without any promoter or additive. The method is highly efficient and environmentally benign with low cost and concise manipulation. Copyright © 2014 John Wiley & Sons, Ltd. 相似文献
6.
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
7.
The asymmetric synthesis of functionalized homoallylic amines and silyl functionalized pyrrolidines through the Lewis acid promoted condensation of chiral (E)-crotylsilanes with sulfonyl imines and in situ generated N-acyl imines is described. We had anticipated that this bond construction could be used in the asymmetric synthesis of the N-terminal amino acid subunit of the nikkomycins. Aryl sulfonyl imines condense with chiral silane reagents in the presence of BF3·OEt2 to form homoallylic arylsulfonyl amines with useful levels of syn selectivity. For cases involving aryl N-acyl imines we have learned that the temperature controls the course of the reaction. For instance, at temperatures of −78°C or below the major product is the pyrrolidine, while at higher temperatures (−30 to −20°C) the homoallylic amine is produced. For the cases studied, the [3+2]-annulation is limited to aryl imine derivatives, as alkyl- and branched- imines failed to produce the pyrrolidine derivatives: higher reaction temperatures promote the conversion of the annulation product to the homoallylic amines. In double stereodifferentiating reactions with in situ generated imines, good levels of selectivity were achieved in the formation of secondary amines bearing syn–anti and syn–syn stereochemical triads. 相似文献
8.
9.
Adiseshu Kattuboina 《Tetrahedron letters》2008,49(23):3722-3724
Chiral N-phosphonyl homoallylic amines were synthesized by the reaction of allylmagnesium bromide with chiral N-phosphonyl imines. The C2-symmetric chiral N-phosphonyl group was optimized for this reaction. Excellent yields and good diastereoselectivities were obtained for eight examples. 相似文献
10.
Gupton JT Telang N Jia X Giglio BC Eaton JE Barelli PJ Hovaizi M Hall KE Welden RS Keough MJ Worrall EF Finzel KL Kluball EJ Kanters RP Smith TM Smith SQ Nunes SR Wright MT Birnstihl JM 《Tetrahedron》2010,66(44):8485-8493
Studies directed at the amine exchange reaction of vinamidinium salts followed by sodium borohydride reduction to secondary and tertiary allylic amines are described. The tertiary allylic amines were alkylated and subjected to base mediated rearrangement to yield a variety of highly functionalized tertiary homoallylic amines. 相似文献
11.
A camphorquinone-derived chiral homoallylic amine was found to react with various aldehydes via imine formation and asymmetric 2-azonia-Cope rearrangement to give optically active homoallylic primary amines. A practical level of enantioselectivity with high functional group tolerance has been attained in this transformation. 相似文献
12.
An asymmetric Lewis acid-mediated [2,3]-sigmatropic rearrangement of allylic amines has been developed, affording the corresponding homoallylic amines in good yield and excellent enantioselectivities. The rearrangement proceeds by complexation of the chiral Lewis acid to the amine followed by deprotonation and rearrangement. 相似文献
13.
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
14.
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
15.
The development of a catalytic asymmetric method for the direct aminoallylation of aldehydes is described that gives high asymmetric inductions for a broad range of substrates including both aromatic and aliphatic aldehydes. This method allows for direct isolation of unprotected analytically pure homoallylic amines without chromatography. The unique catalyst system developed for this process involves the synergistic interaction between a chiral and a nonchiral Br?nsted acid. 相似文献
16.
Zhong‐Lin Tao Alafate Adili Hong‐Cheng Shen Zhi‐Yong Han Liu‐Zhu Gong 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2016,128(13):4394-4398
A highly selective multicomponent carbonyl allylation reaction of 1,3‐butadienes, aryldiazonium tetrafluoroborates, and aldehydes has been established under the combined catalysis of palladium acetate and chiral anion phase transfer to render the favorable assembly of chiral Z‐configured homoallylic alcohols in high yields and with excellent levels of enantioselectivity. 相似文献
17.
Kalyan Kumar Pasunooti 《Tetrahedron letters》2009,50(24):2979-1822
A mild and highly efficient copper-catalyzed, one-pot, three-component reaction is developed for the synthesis of homoallyl amines. Reaction of an aldehyde, a carbamate, and allyltrimethylsilane in the presence of 5 mol % Cu(OTf)2 furnishes the corresponding protected homoallylic amines in good to excellent yields. 相似文献
18.
Catalytic Enantioselective Assembly of Homoallylic Alcohols from Dienes,Aryldiazonium Salts,and Aldehydes
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Zhong‐Lin Tao Alafate Adili Hong‐Cheng Shen Zhi‐Yong Han Prof. Dr. Liu‐Zhu Gong 《Angewandte Chemie (International ed. in English)》2016,55(13):4322-4326
A highly selective multicomponent carbonyl allylation reaction of 1,3‐butadienes, aryldiazonium tetrafluoroborates, and aldehydes has been established under the combined catalysis of palladium acetate and chiral anion phase transfer to render the favorable assembly of chiral Z‐configured homoallylic alcohols in high yields and with excellent levels of enantioselectivity. 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.
[Chemical reaction: See text] A convenient preparation of functionalized chiral tetrahydropyridine-3-carboxylates from nitriles in 68-90% enantiomeric excess (ee) via allylboration, followed by a conjugate addition-elimination and ring-closing metathesis, has been developed. Thus, the treatment of the acetate derived from vinylalumination of formaldehyde by use of [alpha-(ethoxycarbonyl)vinyl]diisobutylaluminum with chiral beta-substituted and beta-unsubstituted homoallylic amines, prepared in >98% diastereomeric excess (de) and 68-90% ee via allylboration of the corresponding N-aluminoimines, furnished functionalized aminodienes, which underwent ring-closing metathesis to provide chiral C5-C6 disubstituted tetrahydropyridine-3-carboxylates. This methodology has been applied for the synthesis of a chiral C6-substituted tetrahydropyridine with known GABA-inhibiting properties at low concentrations. 相似文献