cas 37088-67-8, (R)-3-Amino-3-phenyl propionic acid methylester

Articles about 37088-67-8Total 30 be found

Article title
Article abstract
Author
Journal number and time
Download

Multicomponent Catalytic Enantioselective Synthesis of Isoxazolidin-5-Ones
We report herein a strategy to afford a multicomponent catalytic enantioselective synthesis of β-substituted isoxazolidin-5-ones via a KMC process promoted by a suited cupreine used as bifunctional organocatalyst. The hydroxamic acid component, with a ste
Annibaletto, Julien,Brière, Jean-Fran?ois,Levacher, Vincent,Martzel, Thomas,Oudeyer, Sylvain
supporting information
p. 4447 - 4451
(2021/08/09)

Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected β-Enamino Esters with Trichlorosilane
Catalytic asymmetric reduction of N-unsubstituted β-enamino esters represents a major challenge for asymmetric catalysis. In this paper, the first organocatalytic system that could be used for the asymmetric hydrosilylation of N-unsubstituted β-enamino esters has been developed. Using N-tert-butylsulfinyl-L-proline-derived amides and L-pipecolinic acid-derived formamides as catalyst, a broad range of β-aryl- and β-alkyl-substituted free β-amino esters could be prepared with high yields and enantioselectivities. The practicality was illustrated by the gram-scale asymmetric synthesis of ethyl (R)-3-amino-3-phenylpropanoate and isopropyl (S)-3-amino-4-(2,3,5-trifluorophenyl)butanoate. The resulting product can be smoothly transformed to the FDA approved medicines dapoxetine and sitagliptin in a short synthetic route.
Ye, Jianheng,Wang, Chao,Chen, Lin,Wu, Xinjun,Zhou, Li,Sun, Jian
p. 1042 - 1047
(2016/04/19)

Stereoselective synthesis of activated 2-arylazetidines via imino-aldol reaction
A simple and efficient synthetic route to substituted N-sulfinyl and N-sulfonyl azetidines is described involving imino-aldol reaction of ester enolates with racemic and non-racemic aldimines for obtaining β-amino esters as a key step. These β-amino ester
Ghorai, Manas K.,Das, Subhomoy,Das, Kalpataru,Kumar, Amit
p. 9042 - 9049
(2015/09/01)

Studies on N-activation for the lipase-catalyzed enantioselective preparation of β-amino esters from 4-phenylazetidin-2-one
The effect of N-substitution was examined for the enantio-selective lipase-catalyzed ring-opening reaction of racemic 4-phenylazetidin-2-one with methanol in dry organic solvents. Marked differences in the reactivity of various N-protected 4-phenylazetidin-2-ones were observed. Preparativescale reactions with Candida antarctica lipase B (Novozym 435 preparation) yielded N-acylated methyl (R)-3-amino-3- phenylpropanoates with enantiomeric excess (ee) values >99% in up to a 49% isolated yield, whereas Thermomyces lanuginosus lipase (Lipozyme TM IM) gave enantiomerically enriched methyl (S)-3-acetamido-3-phenylpropanoate. Candida antarctica lipase A catalyzed the cleavage of the N-chloroacetyl protective group, whereas all of the other examined lipases underwent the ring-opening reaction.
Sundell, Riku,Kanerva, Liisa T.
p. 1500 - 1506
(2015/03/04)

METHOD FOR PRODUCING beta-AMINOCARBONYL COMPOUND
An optically active β-aminocarbonyl compound is obtained by a Mannich reaction between an aldimine in which: nitrogen is protected and a malonic acid diester, in the presence of optically active BINOL and dialkyl magnesium (in which two alkyl groups are the same or different) in an amount 1 to 2 molar times the amount of the BINOL.
-
Paragraph 0024

(2013/04/10)

Direct catalytic asymmetric addition of acetonitrile to N-thiophosphinoylimines
Direct catalytic addition of acetonitrile pronucleophiles to thiophosphinoylimines is described. Soft Lewis acid-hard Bronsted base cooperative catalysis is crucial to promote this elusive carbon-carbon bond-forming reaction in an enantioselective fashion
Kawato, Yuji,Kumagai, Naoya,Shibasaki, Masakatsu
p. 11227 - 11229
(2013/11/19)

Enantioselective organocatalytic α-alkylation of ketones by S N1-type reaction of alcohols
The enantioselective α-alkylation reaction of cyclic ketones is described. Our catalyst, based on a "privileged" pyrrolidine ring bearing a chiral thioxotetrahydropyrimidinone ring, is a highly reactive catalyst for cyclic ketones. When this catalyst was coupled with in situ generated carbocations derived from alcohols, the corresponding α-alkylated adducts were obtained in moderate to quantitative yields and low to high enantioselectivities (up to 80% ee). The catalyst loading can be efficiently reduced to 10%, which is the lowest value reported in the literature for such an organocatalytic transformation.
Trifonidou, Maria,Kokotos, Christoforos G.
supporting information; experimental part
p. 1563 - 1568
(2012/04/23)

Triclorosilane-mediated stereoselective synthesis of β-amino esters and their conversion to highly enantiomerically enriched β-lactams
A highly stereoselective trichlorosilane-mediated reduction of N-benzyl enamines was developed; the combination of a low cost, easy to make metal-free catalyst and an inexpensive chiral auxiliary allowed to perform the reaction on substrates with different structural features often with total control of the stereoselectivity. By easy deprotection through hydrogenolysis followed by conversion of β-aminoester to 2-azetidinones, the synthesis of enantiomerically pure β-lactams (>98% e.e.) was successfully accomplished.
Guizzetti, Stefania,Benaglia, Maurizio,Bonsignore, Martina,Raimondi, Laura
p. 739 - 743
(2011/04/22)

Highly practical BINOL-derived acid-base combined salt catalysts for the asymmetric direct mannich-type reaction
The catalytic asymmetric direct Mannich-type reaction between aldimines and 1,3-dicarbonyl compounds is one of the most important carbon-carbon bond-forming reactions in organic chemistry. The resulting Mannich adducts can be efficiently transformed into pharmaceutically useful, optically active -amino ketones, -amino esters, -lactams, etc. In the course of our study of chiral acid-base combined salt catalysts for asymmetric reactions, we developed a series of simple, practical, chiral BINOL-derived salt catalysts, such as chiral pyridinium 1,1-binaphthyl-2,2-disulfonates 1, chiral lithium(I) binaphtholate 2, chiral magnesium(II) binaphtholate (3), chiral calcium(II) phosphate 4, and chiral phosphoric acid 5, which were particularly effective for direct Mannich-type reactions. 1 Introduction 2 1,1-Binaphthyl-2,2-disulfonic Acid (BINSA)-Pyridinium Salts 3 Lithium(I) Binaphtholate Salts 4 Magnesium(II) Binaphtholate Salts 5 Calcium(II) Phosphate Salts and Chiral Phosphoric Acids 6 Conclusions. Georg Thieme Verlag Stuttgart · New York.
Hatano, Manabu,Ishihara, Kazuaki
scheme or table
p. 3785 - 3801
(2011/02/16)

Synthesis and biological evaluation of new jasplakinolide (jaspamide) analogs
Synthesis and biological evaluation of jasplakinolide analogs are described. The synthesis of analogs utilized a diastereoselective syn-aldol reaction and an orthoester Claisen rearrangement as key steps. All synthetic analogs were evaluated for their abi
Ghosh, Arun K.,Dawson, Zachary L.,Moon, Deuk Kyu,Bai, Ruoli,Hamel, Ernest
scheme or table
p. 5104 - 5107
(2010/10/04)

Stereoselective chemoenzymatic preparation of β-amino esters: Molecular modelling considerations in lipase-mediated processes and application to the synthesis of (S)-dapoxetine
A wide range of optically active 3-amino-3-arylpropanoic acid derivatives have been prepared by means of a stereoselective chemoenzymatic route. The key step is the kinetic resolution of the corresponding β-amino esters. Although the enzymatic acylations of the amino group with ethyl methoxyacetate showed synthetically useful enantioselectivities, the hydrolyses of the ester group catalyzed by lipase from Pseudomonas cepacia have been identified as the optimal processes concerning both activity and enantioselectivity. The enantiopreference of this lipase in these reactions has been explained, at the molecular level, by using a fragment-based approach in which the most favoured binding site for a phenyl ring and the most stable conformation of the 3-aminopropanoate core nicely match the (S)-configuration of the major products. The conversion and enantioselectivity values of the enzymatic reactions have been compared in order to understand the influence of the different substitution patterns present in the phenyl ring. This chemoenzymatic route has been successfully applied to the preparation of a valuable intermediate in the synthesis of (S)-dapoxetine, which has been chemically synthesised in excellent optical purity.
Rodriguez-Mata, Maria,Garcia-Urdiales, Eduardo,Gotor-Fernandez, Vicente,Gotor, Vicente
supporting information; experimental part
p. 395 - 406
(2010/06/15)

Photodesulfinylation of optically active N-sulfinyl amines
Photolysis of enantiopure N-sulfinyl amines (sulfinamides) in Et2O-MeOH gives amines in good yield without racemization.
Davis, Franklin A.,Ramachandar, Tokala,Zhang, Yanfeng,Chai, Jing,Qiu, Hui,Deng, Jianghe,Velvadapu, Venkata
experimental part
p. 4042 - 4044
(2010/08/07)

Magnesium(II)-binaphtholate as a practical chiral catalyst for the enantioselective direct mannich-type reaction with malonates
(Equation Presented). A highly enantioselective direct Mannich-type reaction of aldimines with dialkyl malonates was developed with the use of a Mg(II)-BINOLate salt, which was designed as a cooperative acid-base catalyst that can activate both aldimines and malonates. Optically active β-aminoesters and α-halo-β-aminoesters could be synthesized in high yields and with high enantioselectivities. This inexpensive and practical Mg(II)-BINOLate salt could be used in gram-scale catalysis.
Hatano, Manabu,Horibe, Takahiro,Ishihara, Kazuaki
supporting information; experimental part
p. 3502 - 3505
(2010/09/11)

Structures of β-amino ester enolates: New strategies using the method of continuous variation
The solution structures of four enolates derived from β-amino esters are investigated using 6Li NMR spectroscopy in conjunction with the method of continuous variation (method of Job). Ensembles of homo- and heteroaggregated enolates are generated by mixing enantiomers ofa single enolate (R/S mixtures), opposite antipodes of two different en olates (R/S mixtures), and the same antipodes of two different enolates (RIR mixtures). The numbers of observable aggregates and their dependence on the mole fraction of the two enolates confirm the hexamer assignments. Inherent symmetries observable in the 6Li NMR spectra show the stereochemistry of chelation about the hexagonal drum.
Liou, Lara R.,McNeil, Anne J.,Toombes, Gilman E. S.,Collum, David B.
supporting information; experimental part
p. 17334 - 17341
(2009/09/07)

Synthetic and pharmacological studies on new simplified analogues of the potent actin-targeting Jaspamide
In the recent years, we focused our attention on the cyclodepsipeptide Jaspamide 1, an interesting marine metabolite, possessing a potent inhibitory activity against breast and prostate cancer, as a consequence of its ability to disrupt actin cytoskeleton dynamics. Although its biological profile has been well determined, many mechanistic details are still missing in terms of molecular target identification. For this reason, we decided to synthetically modify the natural metabolite, obtaining small arrays of unnatural variants useful to illuminate the structural requirements essential for the activity. Here, we report the synthesis of seven new Jaspamide analogues 2-8, containing, as the parent compound, a β-amino acid in the cyclopeptide backbone. Their biological profile is also described.
Terracciano, Stefania,Bruno, Ines,D'Amico, Elisabetta,Bifulco, Giuseppe,Zampella, Angela,Sepe, Valentina,Smith, Charles D.,Riccio, Raffaele
p. 6580 - 6588
(2008/12/21)

3-AMINO-3-ARYLPROPIONIC ACID n-ALKYL ESTERS, PROCESS FOR PRODUCTION THEREOF, AND PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE 3-AMINO-3-ARYLPROPIONIC ACIDS AND ESTERS OF THE ANTIPODES THERETO
The present invention is to provide an n-alkyl 3-amino-3-arylpropionate represented by the formula (I): wherein Ar1 represents an aryl group which may have a substituent(s), provided that a phenyl group and 4-methoxyphenyl group are excluded, R1 represents an n-propyl group or an n-butyl group, and a process for preparing the same, and its optically active compound and an optically active (S or R)-3-amino-3-arylpropionic acid represented by the formula (III-a): wherein Ar represents an aryl group which may have a substituent(s), and * represents an asymmetric carbon, and a process for preparing an optically active n-alkyl (R or S)-3-amino-3-arylpropionate represented by the formula (IV-a): wherein Ar and R1 have the same meanings as defined above, * represents an asymmetric carbon, provided that it has a reverse absolute configuration to the compound of the formula (III-a).
-
Page/Page column 25-26

(2008/06/13)

Integrin antagonists useful as anticancer agents
The invention relates to compounds of the Formula 1 and to pharmaceutically acceptable salts and solvates thereof, wherein A, X2, X4, X5 and X1 are as defined herein. The invention also relates to methods of tre
-
Page/Page column 35

(2010/11/08)

Copper(I)-fesulphos Lewis acid catalysts for enantioselective Mannich-type reaction of N-sulfonyl imines
Copper(I) complexes of Fesulphos ligands are efficient chiral Lewis acid catalysts in the Mannich-type addition of silyl enol ethers of ketones, esters, and thioesters to N-(2-thienyl)sulfonyl aldimines. The corresponding optically active β-amino carbonyl
Gonzalez, Alvaro Salvador,Arrayas, Ramon Gomez,Carretero, Juan C.
p. 2977 - 2980
(2007/10/03)

Lithium amide assisted asymmetric Mannich-type reactions of menthyl acetate with PMP-aldimines
Matrix presented. A lithium enolate of menthyl acetate added to PMP-imines, in the presence of an equimolar amount of lithium diisopropylamide, affords the Mannich-type addition products in high stereoselectivity.
Hata, Seiji,Iguchi, Mayu,Iwasawa, Tetsuo,Yamada, Ken-Ichi,Tomioka, Kiyoshi
p. 1721 - 1723
(2007/10/03)

Completely diastereoselective aziridination of α,β-unsaturated acids via intramolecular reaction of 3-acetoxyaminoquinazolin-4(3H)-ones
(R)-3-Amino-2-[1-(2-hydroxyethoxy)ethyl]quinazolin-4(3H)-one 10 was prepared in 62% yield without the need for chromatography and O-cinnamoylated; reaction with lead tetra-acetate gave aziridine 12 as a single diastereoisomer in quantitative yield which was converted into the β-amino acid ester 15 corresponding to overall enantioselective addition of ammonia to the double bond of cinnamic acid.
Atkinson, Robert S,Draycott, Richard D,Hirst, David J,Parratt, Martin J,Raynham, Tony M
p. 2083 - 2085
(2007/10/03)

Asymmetric Mannich-type reactions with a chiral acetate: Effect of Lewis acid on activation of aldimine
We introduce here a strategy that enables effective addition of lithium enolates of acetates to aldimines. The new method depends strongly on the use of ortho-alkoxy (or ortho-fluoro) aniline-derived aldimines which found to have a potential effect on the enolate addition. This scope was expanded to the asymmetric process using the chiral acetate, which has optically pure 2,6-bis(2-isopropylphenyl)-3,5-dimethylphenol as a chiral auxiliary with axial chirality. A Lewis acid additive is likely to have a complementary role in the pronounced activation of imine functionalities in the Mannich-type addition of the bulky chiral acetate.
Saito, Susumu,Hatanaka, Keiko,Yamamoto, Hisashi
p. 875 - 887
(2007/10/03)

Asymmetric Mannich-type reactions of aldimines with a chiral acetate
(Formula presented) We introduce here a strategy that enables effective addition of lithium enolates of acetates to aldimines. The new method depends strongly on the use of o-alkoxy (or o-fluoro) aniline-derived aldimines which have been found to have a potential effect on the enolate addition. This scope was expanded to the asymmetric process using the chiral acetate. A Lewis acid additive has a complementary role in the pronounced activation of imine functionalities.
Saito, Susumu,Hatanaka, Keiko,Yamamoto, Hisashi
p. 1891 - 1894
(2007/10/03)

Sulfinimines (THIOOXIMINE S-OXIDES): Asymmetric synthesis of methyl (R)-(+)-?-Phenylalanate from (S)(+)-N-(BENZYLIDENE)-p-Toluenesulfinamide : Benzenepropanoic acid, ?-amino-, (R)-, methyl ester from Benzenesulfinamide, 4-methyl-N-(phenylmethylene)- [S-(E
-
Fanelli, Dean L.,Szewczyk, Joanna M.,Zhang, Yulian,Venkat Reddy,Burns, David M.,Davis, Franklin A.,Unch, James,Hart, David J.
p. 50 - 50
(2017/09/25)

Synthesis and applications of nonracemic β-amino aldehydes to the asymmetric synthesis of piperdines: (+)-Dihydropinidine
New methodology for the enantioselective synthesis of stable N-protected β-amino aldehydes 5 and 6, and their application to the asymmetric synthesis of (+)-2-phenylpiperdine (11) and (+)-dihydropinidine (14) is described.
Davis, Franklin A.,Szewczyk, Joanna M.
p. 5951 - 5954
(2007/10/03)

Asymmetric synthesis of taxol and taxotere side chains by enolate hydroxylation
We report an asymmetric synthesis of the taxol and taxotere side chains by hydroxylation of enolates derived from N-substituted methyl 3-amino-3-phenyl propionate with the oxodiperoxymolybdenum (pyridine) (hexamethyl phosphoric triamide) complex (MoOPH). We report an asymmetric synthesis of the taxol and taxotere side chains by hydroxylation of enolates derived from N-substituted methyl 3-amino-3-phenyl propionate with the oxodiperoxymolybdenum (pyridine) (hexamethyl phosphoric triamide) complex (MoOPH).
Hanessian,Sanceau
p. 621 - 624
(2007/10/03)

95. Asymmetric synthesis of the alkaloids mayfoline and N(1)-Acetyl-N(1)-deoxymayfoline
The total syntheses of the spermidine alkaloids (-)-mayfoline (11) and (+)-N(1)-acetyl-N(1)-deoxymayfoline (12) are described. These macrocyclic lactams belong to the most interesting conjugates of the polyamine derivatives very commonly found in nature. The enantioselective syntheses were achieved through resolution of the methyl 3-amino-3-phenylpropanoate (2) by recrystallization of its (+)-L-tartrate salt. Construction of the 13-membered ring ensued through condensation, reductive ring expansion (internal bond cleavage), and finally a transamidation reaction involving a second ring expansion.
Kuehne, Paul,Linden, Anthony,Hesse, Manfred
p. 1085 - 1094
(2007/10/03)

Asymmetric Synthesis of (R)-(+)-β-Phenylalanine from (S)-(+)-Benzylidene-p-toluenesulfinamide. Regeneration of the Sulfinimine Precursor
-
Davis, Franklin A.,Reddy, Rajarathnam E.,Szewczyk, Joanna M.
p. 7037 - 7039
(2007/10/03)

On the Preparation of β-Amino Acids from α-Amino Acids Using the Arndt-Eistert Reaction: Scope, Limitations and Stereoselectivity. Application to Carbohydrate Peptidation. Stereoselective α-Alkylations of Some β-Amino Acids
The Arndt-Eistert homologation of α-amino acids was studied to determine the stereoselectivity in this reaction by chromatographic up-to-date analytical methods.While carbamate-protected phenylglycine was transformed to the corresponding β-amino acid methyl ester with a stereoselectivity of only 9:1, all other tested amino acid derivatives (Ala, Phe, Ser, Orn, tert-Leu and perhydro-azepine-2-carboxylic acid, suitably protected) were homologated with full retention of configuration (products 9-17).The intermediate diazo ketones 1-8 were purified and characterized by their NMR spectra.When nucleophiles derived from partially protected sugars were present during decomposition of the diazo ketones (derived from amino acids or dipeptides), a strong dependence of the yield (products 21-24) on the degree of steric hindrance of the nucleophilic OH group was observed.Two of the β-amino acids obtained from the homologation reaction were transformed to α-substituted (25-27, 31, 32) and α,α-disubstituted β-amino acid derivatives (28, 29) with excellent selctivities (in most cases, a single diastereoisomer was obtained). - Key Words: β-Amino acids, α-branched/Glycopeptides
Podlech, Joachim,Seebach, Dieter
p. 1217 - 1228
(2007/10/02)

APPROACHES TOWARD THE TOTAL SYNTHESES OF ASTIN A, B, AND C
Two nonessential amino acids, (+)-(S)-2-aminobutanoic acid and the methyl ester of L-β-phenylalanine , were synthesized to provide a tripeptide which will be used in the total syntheses of astins A, B, and C.
Jiang, Jianjun,Schumacher, Kelly K.,Joullie, Madeleine M.,Davis, Franklin A.,Reddy, Rajarathnam E.
p. 2121 - 2124
(2007/10/02)

A convenient diastereoselective total synthesis of andrimid
A convenient diastereoselective synthesis of andrimid was accomplished in a straightforward approach and also several β-substituted cyclic imides were prepared in a facile manner.
Rama Rao,Singh,Varaprasad
p. 4393 - 4396
(2007/10/02)