Enzymatic acylation of cyclobutene and cyclobutane meso-diols at low temperature

Hubert, Cécile; Alexandre, Christian; Huet, François

doi:10.1016/s0957-4166(00)00202-0

Cited by 17 publications

(13 citation statements)

References 7 publications

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“…Mild reduction of 1 with NaBH 4 gave lactone 5 ,9 which was also obtained by Wallace et al by oxidation of 3a 11. The enzymatic acylation of 3a in the presence of Pseudomonas fluorescens lipase predominantly yielded monoacetate (–)‐ 6 ,12 and the enantiomeric excess was increased when this reaction was carried out below room temperature 13. The other enantiomer (+)‐ 6 was available by diacetylation of 3a and subsequent hydrolysis in the presence of the same enzyme 14a.…”

Section: Introductionmentioning

confidence: 58%

“…Various addition reactions to cyclobutene derivatives have been investigated. Bromine addition,29 catalytic hydrogenation,30 and catalytic deuteration31 involving anhydride 1 and catalytic hydrogenation of (–)‐ 6 13 and of 5 32 gave the expected products in high yields. In the case of the catalytic deuteration the major product was the exo isomer (≥96 %).…”

Section: Introductionmentioning

confidence: 98%

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Oxoanion Binding by Guanidiniocarbonylpyrrole Cations in Water: A Combined DFT and MD Investigation

Moiani

Cavallotti

Famulari

et al. 2008

Chemistry A European J

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Structures and properties of nonbonding interactions involving guanidinium-functionalized hosts and carboxylate substrates were investigated by a combination of ab initio and molecular dynamics approaches. The systems under study are on one hand intended to be a model of the arginine-anion bond, so often observed in proteins and nucleic acids, and on the other to provide an opportunity to investigate the influence of molecular structure on the formation of supramolecular complexes in detail. Use of DFT calculations, including extended basis sets and implicit water treatment, allowed us to determine minimum-energy structures and binding enthalpies that compared well with experimental data. Intermolecular forces were found to be mostly due to electrostatic interactions through three hydrogen bonds, one of which is bifurcate, and are sufficiently strong to induce a conformational change in the ligand consisting of a rotation of about 180 degrees around the guanidiniocarbonylpyrrole axis. Free binding energies of the complexes were evaluated through MD simulations performed in the presence of explicit water molecules by use of the molecular mechanics Poisson-Boltzmann solvent accessible surface area (MM-PBSA) and linear interaction energy (LIE) approaches. LIE energies were in quantitative agreement with experimental data. A detailed analysis of the MD simulations revealed that the complexes cannot be described in terms of a single binding structure, but that they are characterized by a significant internal mobility responsible for several low-energy metastable structures.

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Section: Introductionmentioning

confidence: 58%

Section: Introductionmentioning

confidence: 98%

Oxoanion Binding by Guanidiniocarbonylpyrrole Cations in Water: A Combined DFT and MD Investigation

Moiani

Cavallotti

Famulari

et al. 2008

Chemistry A European J

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“…[24] Starting from 1 cis-3,4-sbis(acetyloxymethyl)cyclobutene (2) and trans-3,4-bis(acetyloxymethyl)cyclobutene (3) were synthesized according to two different procedures already reported in the literature as displayed in Scheme 1. [21,22] As expected, all these cyclobutenes were thermally unstable resulting in the formation of dienes by thermal opening of cyclobutenes, which is a long established route. [25] Polymerization Initial polymerization of monomers 2 and 3 was accomplished with initiators I and II as shown in Scheme 1.…”

Section: Monomer Synthesismentioning

confidence: 99%

“…[15][16][17][18][19][20] Herein, we describe the synthesis and the characterization of substituted poly(cyclobutenes) derived from the stereoisomers cis-3,4-bis(acetyloxymethyl)cyclobutene (2) and trans-3,4-bis(acetyloxymethyl)cyclobutene (3). The previously reported [21,22] stereoisomer 2 and the stereoisomer 3, not yet polymerized, were selected in order to allow a better understanding of the effects of the substituents on the regioselectivity and stability of the propagating species during the ROMP of strained cyclic olefins with the ruthenium initiator systems I and II. The activity of initiators I and II was studied by determination of the rates of propagation and the living synthesis of substituted polybutadienes was confirmed using a sequential monomer addition experiment.…”

Section: Introductionmentioning

confidence: 99%

Ring Opening Metathesis Polymerization (ROMP) of cis‐ and trans‐3,4‐Bis(acetyloxymethyl)cyclobut‐1‐enes and Synthesis of Block Copolymers

Lapinte¹,

Frémont²,

Montembault³

et al. 2004

Macro Chemistry & Physics

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Summary: The synthesis and living ring opening metathesis polymerization (ROMP) of diacetate functionalized cyclobutene derivatives cis‐3,4‐bis(acetyloxymethyl)cyclobutene (2) and trans‐3,4‐bis(acetyloxymethyl)cyclobutene (3) were investigated with the functional group tolerant initiators (PCy3)2(Cl)2RuCHPh (I) and (SIMes)(PCy3)(Cl)2RuCHPh (II) (SIMes: 1,3‐dimesityl‐4,5‐dihydroimidazol‐2‐ylidene). The kinetic parameters of the ROMP initiated by the ruthenium alkylidene complexes I and II were determined and correlated to monomer stereochemistry. The cis isomer 2 was found to be more reactive than the trans isomer 3 and to generate functional polymers of narrow molecular weight distribution especially with the classical “first generation Grubbs catalyst” I. Block copolymers containing 2 and cyclooctadiene (COD) or norbornene (NBE) were synthesized. Block copolymer poly(2‐b‐COD) was hydrolyzed and converted to a material with a block bearing hydrophilic alcohol functional groups and hydrophobic block.SEC elution profiles: poly(2) prepolymer and block copolymer poly(2‐b‐COD).magnified imageSEC elution profiles: poly(2) prepolymer and block copolymer poly(2‐b‐COD).

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“…( 8,124.5,70.5,69.0,59.2,56.5,47.4,43.5,39.9. HRMS: C 9 13 C NMR (125 MHz, CD 3 OD) δ 149.0, 124. 2, 70.9, 70.9, 60.7, 56.5, 50.5, 45.2, 44.4.…”

Section: Tert-butyl-(1-(((1s4r)-4-((tert-butyldiphenylsilyloxy) Methmentioning

confidence: 99%

Synthesis of Novel Triazolo Cyclobutane Nucleoside Analogs

Tran

Ngo

Dinh

et al. 2015

Bulletin Korean Chem Soc

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Enzymatic acylation of cyclobutene and cyclobutane meso-diols at low temperature

Cited by 17 publications

References 7 publications

Oxoanion Binding by Guanidiniocarbonylpyrrole Cations in Water: A Combined DFT and MD Investigation

Oxoanion Binding by Guanidiniocarbonylpyrrole Cations in Water: A Combined DFT and MD Investigation

Ring Opening Metathesis Polymerization (ROMP) of cis‐ and trans‐3,4‐Bis(acetyloxymethyl)cyclobut‐1‐enes and Synthesis of Block Copolymers

Synthesis of Novel Triazolo Cyclobutane Nucleoside Analogs

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