Stereoselective synthesis of (E)-3,3-diaryl and (E)-3-aryl-3-aryloxy allylamines and allylalcohols from trans-cinnamyl chloride and alcohol

Limberger, Jones; Claudino, Thiago S.; Monteiro, Adriano L.

doi:10.1039/c4ra08036j

Cited by 6 publications

(3 citation statements)

References 33 publications

(29 reference statements)

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“…5b 32 – 34 . The ( E )-vinyl bromide 6 , prepared from trans -cinnamyl chloride 35 , was coupled with aryl boronic acid 7 to afford the diastereopure ( E )-allylic amine 8 in 91% yield. A sequential addition of catalyst, hydrogen donor, and strong acid afforded the desired ( R )-Tolterodine in 88% overall yield and 96.0:4.0 er.…”

Section: Resultsmentioning

confidence: 99%

Asymmetric synthesis of γ-branched amines via rhodium-catalyzed reductive amination

2018

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Amines bearing γ-stereocenters are highly important structural motifs in many biologically active compounds. However, reported enantioselective syntheses of these molecules are indirect and often require multiple steps. Herein, we report a general asymmetric route for the one-pot synthesis of chiral γ-branched amines through the highly enantioselective isomerization of allylamines, followed by enamine exchange and subsequent chemoselective reduction. This protocol is suitable for establishing various tertiary stereocenters, including those containing dialkyl, diaryl, cyclic, trifluoromethyl, difluoromethyl, and silyl substituents, which allows for a rapid and modular synthesis of many chiral γ-branched amines. To demonstrate the synthetic utility, Terikalant and Tolterodine are synthesized using this method with high levels of enantioselectivity.

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Section: Resultsmentioning

confidence: 99%

Asymmetric synthesis of γ-branched amines via rhodium-catalyzed reductive amination

2018

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“…(2 E )‐3‐(4‐chlorophenyl)‐3‐phenylprop‐2‐en‐1‐ol ( Yj ) (for 4j ) was prepared by the Suzuki cross‐coupling reaction of ( E )‐3‐bromo‐3‐phenylprop‐2‐en‐1‐ol and 4‐chlorophenylboronic acid by the literature method …”

Section: Methodsmentioning

confidence: 99%

“…(2E)-3-(4-chlorophenyl)-3-phenylprop-2-en-1-ol (Yj) (for 4j) was prepared by the Suzuki cross-coupling reaction of (E)-3-bromo-3phenylprop-2-en-1-ol and 4-chlorophenylboronic acid by the literature method. [34] The 3,3-diaryl-2-propen-1-amines 4a-k were prepared from the corresponding alcohols Ya, Yc-k. The corresponding bromides were prepared by reaction of the alcohols with PBr 3 in ether and used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Intramolecular Cyclization of 3,3‐Diarylpropenylamides of Electron‐Deficient Alkenes: Stereoselective Synthesis of Functionalized Hexahydrobenzo[f]isoindoles

Sugiura

Yamazaki

2018

Eur J Org Chem

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Intramolecular Diels–Alder reactions of various 3,3‐diarylpropenylamides of electron‐deficient alkenes to give hexahydrobenzo[f]isoindoles were investigated. Reaction of 1,1,2‐ethenetricarboxylic acid 1,1‐diethyl ester with 3,3‐diaryl‐2‐propen‐1‐amines under the amide formation conditions gave the tricyclic compounds in sequential processes involving intramolecular Diels–Alder reaction. The reaction gave cis‐ and trans‐fused tricyclic compounds selectively, depending on the substituents on the benzene ring, reaction temperature and solvent. In the reaction with dissymmetrically substituted 3,3‐diaryl‐2‐propen‐1‐amines, trans‐substituted aryl group reacted mainly as a styrene component. Amides of electron‐deficient alkenic carboxylic acids such as fumarate do not undergo cyclization at room temperature sequentially and the reaction on heating gave trans‐fused hexahydrobenzo[f]isoindoles. The origin of the observed stereoselectivity has been examined by the DFT calculations.

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ChemInform Abstract: Stereoselective Synthesis of (E)‐3,3‐Diaryl and (E)‐3‐Aryl‐3‐aryloxy Allylamines and Allylalcohols from trans‐Cinnamyl Chloride and Alcohol.

2015

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Stereoselective Synthesis of (E)-3,3-Diaryl and (E)-3-Aryl-3-aryloxy Allylamines and Allylalcohols from trans-CinnamylChloride and Alcohol. -Vinyl bromides (I) are used as substrates in cross-coupling reactions furnishing arylated products (III) and (V) in good to excellent yields and complete retention of the (E)-configuration. -(LIMBERGER, J.; CLAUDINO, T. S.; MONTEIRO*, A. L.; RSC Adv. 4 (2014) 85, 45558-45565, http://dx.doi.org/10.1039/C4RA08036J ; Lab. Mol. Catal., Inst. Quim., 91501 Porto Alegre, Rio Grande do Sul, Brazil; Eng.) -M. Paetzel 13-034

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Stereoselective synthesis of (E)-3,3-diaryl and (E)-3-aryl-3-aryloxy allylamines and allylalcohols from trans-cinnamyl chloride and alcohol

Abstract: Syntheses of (E)-3,3-diaryl and (E)-3-aryl-3-aryloxy allylamines and allylalcohols based on bromination/dehydrobromination sequences followed by Suzuki cross-coupling or Ullmann vinylation were achieved.

Cited by 6 publications

References 33 publications

Asymmetric synthesis of γ-branched amines via rhodium-catalyzed reductive amination

Asymmetric synthesis of γ-branched amines via rhodium-catalyzed reductive amination

Intramolecular Cyclization of 3,3‐Diarylpropenylamides of Electron‐Deficient Alkenes: Stereoselective Synthesis of Functionalized Hexahydrobenzo[f]isoindoles

ChemInform Abstract: Stereoselective Synthesis of (E)‐3,3‐Diaryl and (E)‐3‐Aryl‐3‐aryloxy Allylamines and Allylalcohols from trans‐Cinnamyl Chloride and Alcohol.

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