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Cas Database

100017-29-6

100017-29-6

Identification

  • Product Name:dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate

  • CAS Number: 100017-29-6

  • EINECS:

  • Molecular Weight:262.306

  • Molecular Formula: C15H18O4

  • HS Code:

  • Mol File:100017-29-6.mol

Synonyms:dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate

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Relevant articles and documentsAll total 7 Articles be found

Enantioselective allylic alkylation catalyzed by novel C2-symmetric bisphosphinites

G?k, Ya?ar,Zeki G?k, Halil

, p. 490 - 495 (2015)

In this article, we present our results concerning new C2-symmetric bisphosphinites with a (1R,2R)-1,2-bis([1,1: 3,1-terphenyl]-5-yl)ethane backbone. For the given chirality of the backbone, derivatives with aromatic and aliphatic substituents

Asymmetric Allylic Alkylation Catalyzed by Palladium-Sparteine Complexes

Togni, Antonio

, p. 683 - 690 (1991)

The cationic complex 3-C3H5)(sparteine)>PF6 (6) was found to be a suitable catalyst precursor for the asymmetric alkylation of allylic acetates with Na as the nucleophile.This constitutes one of the first and still rare examples of a phosphine-free system for this type of Pd-catalyzed reaction.Using 5 mol percent of 6, alkylation products were obtained in up to 90 percent isolated yield and 85 percent enantiomeric excess.The alkylation reaction was shown to occur with overall retention of configuration, indicating an analogous mechanism to the one previouslyproposed for phosphine-containing catalysts.The reactivity of allylic acetates is strongly dependent upon the nature of the substituents, open-chain aliphatic substrates being unreactive.

Palladium-catalyzed enantioselective allylic substitution in the presence of monodentate furanoside phosphoramidites

Majdecki, Maciej,Jurczak, Janusz,Bauer, Tomasz

, p. 799 - 807 (2015/03/14)

A library of monodentate furanoside phosphoramidites, easily synthesized from inexpensive D-xylose and optically pure 1,1-bi-2-naphthol (BINOL), was used as ligands for the palladium-catalyzed allylic alkylation and amination. The matched pair was formed from D-xylose-derivatives and (S)-BINOL. The asymmetric induction depends strongly on the substituent at the C5 of the carbohydrate backbone; both bulky 5-O-pivaloyl and 5-deoxy derivatives gave excellent results, whereas ligands with trityl protection at position C5 induced low ee values with reversal of configuration. The solvent used for the addition is also of great importance with highest enantioselectivities observed in diethyl ether. The best results for both alkylation and amination, up to 98-99 ee, were obtained for sterically demanding allylic acetates. Single is better: New carbohydrate ligands bearing a single 1,1-bi-2-naphthol (BINOL)-derived phosphoramidite moiety are developed and successfully applied to the palladium-catalyzed asymmetric allylic substitution. The enantioselectivities are equal or better than those obtained for similar systems containing two BINOL moieties and reach up to 99 ee.

Effective chiral ferrocenyl phosphine-thioether ligands in enantioselective palladium-catalyzed allylic alkylations

Cheung, Hong Yee,Yu, Wing-Yiu,Au-Yeung, Terry T. L.,Zhou, Zhongyuan,Chan, Albert S. C.

experimental part, p. 1412 - 1422 (2009/12/22)

Chiral ferrocene-derived phosphine-thioether mixed donor ligands supported by heterocycles effected the palladium-catalyzed enantioselective allylic alkylations with excellent yields and enantioselectivities (up to 96% ee). With cyclic and unsymmetrical a

Highly diastereoselective synthesis of 2,6-di[1-(2-alkylaziridin-1-yl) alkyl]pyridines, useful ligands in palladium-catalyzed asymmetric allylic alkylation

Savoia, Diego,Alvaro, Giuseppe,Di Fabio, Romano,Fiorelli, Claudio,Gualandi, Andrea,Monari, Magda,Piccinelli, Fabio

, p. 1883 - 1893 (2007/10/03)

C2-Symmetrical, enantiopure 2,6-di[1-(1-aziridinyl)alkyl] pyridines (DIAZAPs) were prepared by a high-yielding, three-step sequence starting from 2,6-pyridinedicarbaldehyde and (S)-valinol or (S)-phenylglycinol. The new compounds were tested as

Palladium complexes with chiral diphospholane ligands: Comparative catalytic properties and analysis of (η3-allyl)palladium species

Malaise, Gregory,Ramdeehul, Shailesh,Osborn, John A.,Barloy, Laurent,Kyritsakas, Nathalie,Graff, Roland

, p. 3987 - 4001 (2007/10/03)

The chiral diphospholane ligands Duphos (1) and Duxantphos (2), which can be differentiated by their bite angle, were applied to palladium-catalysed asymmetric reactions, essentially allylic alkylations with symmetrically (3a-d) or unsymmetrically (5a,b) substituted allylic acetates as substrates. The most interesting results were found with the first series of substrates in which 2 was more reactive and/or selective than 1. The model complexes of the catalytic intermediates [Pd{(S,S)-1}(η3-cyclohexenyl)](BF4) (10) and exo-[Pd{(R,R)-(η3-cyclohexenyl)](SbF6) (11) could be characterised by X-ray crystallography. 1H and 32P NMR spectroscopic analyses of [Pd{(R,R)-2}(η3-diphenylallyl)] (SbF6) (12) and [Pd{(R,R)-2}(η3-allyl)](SbF 6) (13) revealed the presence of exchanging isomers in solution. Structural data provided by these techniques combined with the preferential rotation model led to a satisfactory interpretation of the catalytic allylic alkylation results. It appears that the bite angle plays a crucial role in the positioning of the proximal methyl groups, which determines the distribution of allyl isomeric intermediates and the balance between clockwise and anticlockwise rotations in the enantioselective step. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Process route upstream and downstream products

Process route

(rac)-(E)-2-acetoxy-4-phenylbut-3-ene
82045-04-3

(rac)-(E)-2-acetoxy-4-phenylbut-3-ene

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

(E)-dimethyl 2-(4-phenylbut-3-en-2-yl)malonate
200191-40-8

(E)-dimethyl 2-(4-phenylbut-3-en-2-yl)malonate

dimethyl <1-phenyl-2(E)-butenyl>malonate
115404-72-3

dimethyl <1-phenyl-2(E)-butenyl>malonate

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate
100017-29-6

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate

Conditions
Conditions Yield
With N,O-bis-(trimethylsilyl)-acetamide; bis(μ-trifluoroacetato)bis{(2,3,4,-η)-3-pentenyl}dipalladium; 2-<(1R)-2-endo-1,7,7-trimethylbicyclo<2.2.1>hept-2-yl>-1,10-phenanthroline; potassium acetate; In tetrahydrofuran; at 25 ℃; Title compound not separated from byproducts;
malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

ethyl (E)-3-phenyl-1-methylprop-1-enyl carbonate
163807-60-1

ethyl (E)-3-phenyl-1-methylprop-1-enyl carbonate

(E)-dimethyl 2-(4-phenylbut-3-en-2-yl)malonate
200191-40-8

(E)-dimethyl 2-(4-phenylbut-3-en-2-yl)malonate

dimethyl <1-phenyl-2(E)-butenyl>malonate
115404-72-3

dimethyl <1-phenyl-2(E)-butenyl>malonate

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate
100017-29-6

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate

Conditions
Conditions Yield
With 2,6-bis((S)-1-((S)-2-isopropylaziridin-1-yl)(phenyl)methyl)pyridine; potassium acetate; bis-(trimethylsilyl)acetamide; In dichloromethane; at 25 ℃; for 24h; Title compound not separated from byproducts;
(rac)-(E)-2-acetoxy-4-phenylbut-3-ene
82045-04-3

(rac)-(E)-2-acetoxy-4-phenylbut-3-ene

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

dimethyl <1-phenyl-2(E)-butenyl>malonate
115404-72-3

dimethyl <1-phenyl-2(E)-butenyl>malonate

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate
100017-29-6

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate

(R)-2-(1-methyl-3-phenylallyl)malonic acid dimethyl ester
90383-10-1

(R)-2-(1-methyl-3-phenylallyl)malonic acid dimethyl ester

(S,E)-2-(1-methyl-3-phenyl-allyl)malonic acid dimethyl ester
88057-04-9

(S,E)-2-(1-methyl-3-phenyl-allyl)malonic acid dimethyl ester

Conditions
Conditions Yield
With sodium hydride; 4,5-bis[(2R,5R)-2,5-dimethylphospholanyl]-9,9-dimethylxanthene; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; at 20 ℃; for 24h; Further Variations:; Reagents; Solvents; Reaction partners; time; Product distribution;
(rac)-(E)-2-acetoxy-4-phenylbut-3-ene; With bis(η3-allyl-μ-chloropalladium(II)); C33H31FeN2PS; In dichloromethane; acetonitrile; for 0.0833333h; Inert atmosphere;
malonic acid dimethyl ester; With N,O-bis-(trimethylsilyl)-acetamide; lithium acetate; In dichloromethane; acetonitrile; at 20 ℃; for 3h; enantioselective reaction; Inert atmosphere;
(rac)-(E)-2-acetoxy-4-phenylbut-3-ene; With N,O-bis-(trimethylsilyl)-acetamide; bis(η3-allyl-μ-chloropalladium(II)); C35H38NO5P; lithium acetate; In dichloromethane; for 1h; Schlenk technique; Inert atmosphere;
malonic acid dimethyl ester; In dichloromethane; for 24h; Overall yield = 36 %; Schlenk technique; Inert atmosphere;
45 % ee
32 % ee
(rac)-(E)-2-acetoxy-4-phenylbut-3-ene
82045-04-3

(rac)-(E)-2-acetoxy-4-phenylbut-3-ene

dimethyl malonate sodium salt
18424-76-5

dimethyl malonate sodium salt

dimethyl <1-phenyl-2(E)-butenyl>malonate
115404-72-3

dimethyl <1-phenyl-2(E)-butenyl>malonate

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate
100017-29-6

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate

Conditions
Conditions Yield
With 3-C3H5)(sparteine)>PF6; In tetrahydrofuran; for 72h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;
malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

dimethyl <1-phenyl-2(E)-butenyl>malonate
115404-72-3

dimethyl <1-phenyl-2(E)-butenyl>malonate

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate
100017-29-6

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate

Conditions
Conditions Yield
(E)-1-acetoxy-1-phenyl-2-butene; With bis(η3-allyl-μ-chloropalladium(II)); (1R,2R)-1,2-di(1,1’:3’,1’’-terphenyl-5’-yl)ethane-1,2-diyl bis[diphenyl(phosphinite)]; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere; Schlenk technique;
malonic acid dimethyl ester; With N,O-bis-(trimethylsilyl)-acetamide; lithium acetate; In dichloromethane; at 20 ℃; for 16h; Overall yield = 25 %; enantioselective reaction; Inert atmosphere; Schlenk technique;
67 % ee
(E)-1-acetoxy-1-phenyl-2-butene; With bis(η3-allyl-μ-chloropalladium(II)); (1R,2R)-1,2-di(1,1’:3’,1’’-terphenyl-5’-yl)ethane-1,2-diyl bis[dicyclohexyl(phosphinite)]; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere; Schlenk technique;
malonic acid dimethyl ester; With N,O-bis-(trimethylsilyl)-acetamide; lithium acetate; In dichloromethane; at 20 ℃; for 16h; Solvent; Overall yield = 35 %; Catalytic behavior; Inert atmosphere; Schlenk technique;
18 % ee
(rac)-(E)-2-acetoxy-4-phenylbut-3-ene
82045-04-3

(rac)-(E)-2-acetoxy-4-phenylbut-3-ene

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

(E)-dimethyl 2-(4-phenylbut-3-en-2-yl)malonate
200191-40-8

(E)-dimethyl 2-(4-phenylbut-3-en-2-yl)malonate

dimethyl <1-phenyl-2(E)-butenyl>malonate
115404-72-3

dimethyl <1-phenyl-2(E)-butenyl>malonate

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate
100017-29-6

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate

Conditions
Conditions Yield
With N,O-bis-(trimethylsilyl)-acetamide; bis(μ-trifluoroacetato)bis{(2,3,4,-η)-3-pentenyl}dipalladium; 2-<(1R)-2-endo-1,7,7-trimethylbicyclo<2.2.1>hept-2-yl>-1,10-phenanthroline; potassium acetate; In tetrahydrofuran; at 25 ℃; Title compound not separated from byproducts;
malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

ethyl (E)-3-phenyl-1-methylprop-1-enyl carbonate
163807-60-1

ethyl (E)-3-phenyl-1-methylprop-1-enyl carbonate

(E)-dimethyl 2-(4-phenylbut-3-en-2-yl)malonate
200191-40-8

(E)-dimethyl 2-(4-phenylbut-3-en-2-yl)malonate

dimethyl <1-phenyl-2(E)-butenyl>malonate
115404-72-3

dimethyl <1-phenyl-2(E)-butenyl>malonate

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate
100017-29-6

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate

Conditions
Conditions Yield
With 2,6-bis((S)-1-((S)-2-isopropylaziridin-1-yl)(phenyl)methyl)pyridine; potassium acetate; bis-(trimethylsilyl)acetamide; In dichloromethane; at 25 ℃; for 24h; Title compound not separated from byproducts;
(rac)-(E)-2-acetoxy-4-phenylbut-3-ene
82045-04-3

(rac)-(E)-2-acetoxy-4-phenylbut-3-ene

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

dimethyl <1-phenyl-2(E)-butenyl>malonate
115404-72-3

dimethyl <1-phenyl-2(E)-butenyl>malonate

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate
100017-29-6

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate

(R)-2-(1-methyl-3-phenylallyl)malonic acid dimethyl ester
90383-10-1

(R)-2-(1-methyl-3-phenylallyl)malonic acid dimethyl ester

(S,E)-2-(1-methyl-3-phenyl-allyl)malonic acid dimethyl ester
88057-04-9

(S,E)-2-(1-methyl-3-phenyl-allyl)malonic acid dimethyl ester

Conditions
Conditions Yield
With sodium hydride; 4,5-bis[(2R,5R)-2,5-dimethylphospholanyl]-9,9-dimethylxanthene; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; at 20 ℃; for 24h; Further Variations:; Reagents; Solvents; Reaction partners; time; Product distribution;
(rac)-(E)-2-acetoxy-4-phenylbut-3-ene; With bis(η3-allyl-μ-chloropalladium(II)); C33H31FeN2PS; In dichloromethane; acetonitrile; for 0.0833333h; Inert atmosphere;
malonic acid dimethyl ester; With N,O-bis-(trimethylsilyl)-acetamide; lithium acetate; In dichloromethane; acetonitrile; at 20 ℃; for 3h; enantioselective reaction; Inert atmosphere;
(rac)-(E)-2-acetoxy-4-phenylbut-3-ene; With N,O-bis-(trimethylsilyl)-acetamide; bis(η3-allyl-μ-chloropalladium(II)); C35H38NO5P; lithium acetate; In dichloromethane; for 1h; Schlenk technique; Inert atmosphere;
malonic acid dimethyl ester; In dichloromethane; for 24h; Overall yield = 36 %; Schlenk technique; Inert atmosphere;
45 % ee
32 % ee
(rac)-(E)-2-acetoxy-4-phenylbut-3-ene
82045-04-3

(rac)-(E)-2-acetoxy-4-phenylbut-3-ene

dimethyl malonate sodium salt
18424-76-5

dimethyl malonate sodium salt

dimethyl <1-phenyl-2(E)-butenyl>malonate
115404-72-3

dimethyl <1-phenyl-2(E)-butenyl>malonate

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate
100017-29-6

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate

Conditions
Conditions Yield
With 3-C3H5)(sparteine)>PF6; In tetrahydrofuran; for 72h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;
malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

dimethyl <1-phenyl-2(E)-butenyl>malonate
115404-72-3

dimethyl <1-phenyl-2(E)-butenyl>malonate

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate
100017-29-6

dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate

Conditions
Conditions Yield
(E)-1-acetoxy-1-phenyl-2-butene; With bis(η3-allyl-μ-chloropalladium(II)); (1R,2R)-1,2-di(1,1’:3’,1’’-terphenyl-5’-yl)ethane-1,2-diyl bis[diphenyl(phosphinite)]; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere; Schlenk technique;
malonic acid dimethyl ester; With N,O-bis-(trimethylsilyl)-acetamide; lithium acetate; In dichloromethane; at 20 ℃; for 16h; Overall yield = 25 %; enantioselective reaction; Inert atmosphere; Schlenk technique;
67 % ee
(E)-1-acetoxy-1-phenyl-2-butene; With bis(η3-allyl-μ-chloropalladium(II)); (1R,2R)-1,2-di(1,1’:3’,1’’-terphenyl-5’-yl)ethane-1,2-diyl bis[dicyclohexyl(phosphinite)]; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere; Schlenk technique;
malonic acid dimethyl ester; With N,O-bis-(trimethylsilyl)-acetamide; lithium acetate; In dichloromethane; at 20 ℃; for 16h; Solvent; Overall yield = 35 %; Catalytic behavior; Inert atmosphere; Schlenk technique;
18 % ee

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