DOI: 10.5061/dryad.w9ghx3g2t
title: Data from: Catalytic enantioselective synthesis of oxazolines with vinylogous isocyano esters

description: Vinylogous isocyano esters have been prepared for the first time. They
 react with aldehydes to give chiral oxazolines bearing a pendant
 conjugated ester under synergistic silver/organocatalysis. The reaction is
 carried out using a bifunctional squaramide in combination with silver
 oxide and performs well with a number of aryl-, heteroaryl-, and
 cycloalkyl aldehydes, providing the expected heterocycles in good yields
 with good diastereoselectivity and enantiomeric excesses ranging from 60%
 to 95% ee. All new compounds have been characterized by NMR and other
 spectroscopic techniques. Raw NMR data (fid) for all new compounds
 prepared in this work are provided in the data set.
description: NMR spectra were recorded using a Bruker Avance III 300 or Bruker
 Neo500 at, respectively, 300 MHz, or 500 MHz
 for <sup>1</sup>H, or 75 MHz, or 125 MHz for
 <sup>13</sup>C and were processed using MestreNova
 software.
description: # Data from: Catalytic enantioselective synthesis of oxazolines with
 vinylogous isocyano esters
 [https://doi.org/10.5061/dryad.w9ghx3g2t](https://doi.org/10.5061/dryad.w9ghx3g2t) 1H NMR, 13C NMR and DEPT spectra are used to describe the structure of all new compounds prepared in the publication: Catalytic enantioselective synthesis of oxazolines with vinylogous isocyano esters ([https://doi.org/10.1021/acs.orglett.5c02729](https://doi.org/10.1021/acs.orglett.5c02729)) ## Description of the data and file structure Data for each compound are included in a folder named with the compound number designated in the manuscript and/or SI, as “compound number.zip”: * compound_2a.zip * compound_2b.zip * compound_2c.zip * compound_2d.zip * compound_2e.zip * compound_2f.zip * compound_3aa.zip * compound_3ab.zip * compound_3ac.zip * compound_3ad.zip * compound_3ae.zip * compound_3ba.zip * compound_3ca.zip * compound_3da.zip * compound_3ea.zip * compound_3fa.zip * compound_3ga.zip * compound_3ha.zip * compound_3ia.zip * compound_3ja.zip * compound_3ka.zip * compound_3la.zip * compound_3ma.zip * compound_3me.zip * compound_3na.zip * compound_3oa.zip * compound_3pa.zip * compound_3qa.zip * compound_3ra.zip * compound_3rc.zip * compound_3rd.zip * compound_3re.zip * compound_3sa.zip * compound_3ta.zip * compound_4.zip * compound_5aa.zip * compound_5ra.zip * compound_6.zip * ethyl_4-formamidobut-2-enoate_(S5).zip * methyl_4-(terbutoxycarbonylamino)-3-methylbut-2-enoate_(S8).zip * methyl_4-amino-4-oxbut-2-enoate_(S4).zip * methyl_4-formamido-2-metilbut-2-enoate_(S6).zip * methyl_4-formamido-3-methylbut-2-enoate_(S10).zip * methyl-4-formamidopent-2-enoate_(S14).zip * N-1-hydroxypropan-2-yl_formamide_(S12).zip * N-allylformamide_(S2).zip Each zip folder contains two or three sub-folders containing data for 1H NMR (named 1H), 13C NMR (named 13C) and DEPT (named DEPT, when available) spectra, respectively, for the compound indicated in the file name. Each of these sub-folders includes files that contain the raw NMR data (fid) and other files indicating acquisition and processing parameters and spectrum data. Data in JCAMP-DX open file format are also provided within each sub-folder. These files are named as proton.jcamp, carbon.jcamp and dept.jcamp (when available). Accessing this data will allow users to view NMR spectra interactively.  **Abbreviations used are as follows:** NMR: nuclear magnetic resonance SI: supporting information (meaning, Supplementary Materials document) ### The full name of the compounds represented by the compound number N-allylformamide (S2) Methyl (E)-4-amino-4-oxobut-2-enoate (S4) Methyl (E)-4-isocyanobut-2-enoate (2a) Ethyl (E)-4-formamidobut-2-enoate (S5) Ethyl (E)-4-isocyanobut-3-enoate (2b) Methyl (E)-4-formamido-2-methylbut-2-enoate (S6) Methyl (E)-4-isocyano-2-methylbut-2-enoate (2c) Methyl (E)-4-((tert-butoxycarbonyl)amino)-3-methylbut-2-enoate (S8) Methyl (E)-4-formamido-3-methylbut-2-enoate (S10) Methyl (E)-4-isocyano-3-methylbut-2-enoate (2d) N-(1-hydroxypropan-2-yl)formamide (S12) Methyl (E)-4-formamidopent-2-enoate (S14) Methyl (E)-4-isocyanopent-3-enoate (2e) Synthesis of methyl 4-isocyanobutanoate (2f) Methyl (E)-3-((4R,5R)-5-phenyl-4,5-dihydrooxazol-4-yl)acrylate (3aa) Methyl (E)-3-((4R,5R)-5-(p-tolyl)-4,5-dihydrooxazol-4-yl)acrylate (3ba) Methyl (E)-3-((4R,5R)-5-(4-methoxyphenyl)-4,5-dihydrooxazol-4-yl)acrylate (3ca) Methyl (E)-3-((4R,5R)-5-(4-chlorophenyl)-4,5-dihydrooxazol-4-yl)acrylate (3da) Methyl (E)-3-((4R,5R)-5-(4-bromophenyl)-4,5-dihydrooxazol-4-yl)acrylate (3ea) Methyl (E)-3-((4R,5R)-5-(4-nitrophenyl)-4,5-dihydrooxazol-4-yl)acrylate (3fa) Methyl (E)-3-((4R,5R)-5-(m-tolyl)-4,5-dihydrooxazol-4-yl)acrylate (3ga) Methyl (E)-3-((4R,5R)-5-(o-tolyl)-4,5-dihydrooxazol-4-yl)acrylate (3ha) Methyl (E)-3-((4R,5R)-5-(2-methoxyphenyl)-4,5-dihydrooxazol-4-yl)acrylate (3ia) Methyl (E)-3-((4R,5R)-5-(2-chlorophenyl)-4,5-dihydrooxazol-4-yl)acrylate (3ja) Methyl (E)-3-((4R,5S)-5-(furan-2-yl)-4,5-dihydrooxazol-4-yl)acrylate (3ka) Methyl (E)-3-((4R,5R)-5-(furan-3-yl)-4,5-dihydrooxazol-4-yl)acrylate (3la) Methyl (E)-3-((4R,5R)-5-(thiophen-3-yl)-4,5-dihydrooxazol-4-yl)acrylate (3ma) Methyl (E)-3-((4R,5R)-5-(naphthalen-2-yl)-4,5-dihydrooxazol-4-yl)acrylate (3na) Methyl (E)-3-((4R,5R)-5-phenethyl-4,5-dihydrooxazol-4-yl)acrylate (3oa) Methyl (E)-3-((4R,5R)-5-cyclopropyl-4,5-dihydrooxazol-4-yl)acrylate (3pa) Methyl (E)-3-((4R,5R)-5-cyclopentyl-4,5-dihydrooxazol-4-yl)acrylate (3qa) Methyl (E)-3-((4R,5R)-5-cyclohexyl-4,5-dihydrooxazol-4-yl)acrylate (3ra) Methyl (E)-3-((4R,5R)-5-isopropyl-4,5-dihydrooxazol-4-yl)acrylate (3sa) Methyl (E)-3-((4R,5R)-5-(tert-butyl)-4,5-dihydrooxazol-4-yl)acrylate (3ta) Ethyl (E)-3-((4R,5R)-5-phenyl-4,5-dihydrooxazol-4-yl)acrylate (3ab) Methyl (E)-2-methyl-3-((4R,5R)-5-phenyl-4,5-dihydrooxazol-4-yl)acrylate (3ac) Methyl (E)-3-((4R,5R)-5-cyclohexyl-4,5-dihydrooxazol-4-yl)-2-methylacrylate (3rc) Methyl (E)-3-((4R,5R)-5-phenyl-4,5-dihydrooxazol-4-yl)but-2-enoate (3ad) Methyl (E)-3-((4R,5R)-5-cyclohexyl-4,5-dihydrooxazol-4-yl)but-2-enoate (3rd) Methyl (E)-3-((4R,5R)-4-methyl-5-phenyl-4,5-dihydrooxazol-4-yl)acrylate (3ae) Methyl (E)-3-((4R,5R)-4-methyl-5-(thiophen-3-yl)-4,5-dihydrooxazol-4-yl)acrylate (3me) Methyl (E)-3-((4R,5R)-5-cyclohexyl-4-methyl-4,5-dihydrooxazol-4-yl)acrylate (3re) Methyl 3-((4R,5R)-5-phenyl-4,5-dihydrooxazol-4-yl)propanoate (4) Methyl (4R,5R)-4-formamido-5-hydroxy-5-phenylpentanoate (5aa) Methyl (4R,5R)-4-formamido-5-hydroxy-5-cyclohexyl (5ra) Methyl (R)-5-hydroxy-4-oxo-5-phenylpentanoate (6) ## Sharing/access Information NMR data will be available as images in the SI for this manuscript at [https://doi.org/10.1021/acs.orglett.5c02729](https://doi.org/10.1021/acs.orglett.5c02729). ## Code/Software Processed files with extension .fid are ready to be viewed in NMRViewJ or MestReNova. Files with extension .jcamp can be readed and processed with unlicensed software such as JSpecView, ACD/Labs NMR Processor or free online viewers such as NMRium