Data underpinning "Isoselenourea-Catalyzed Enantioselective Pyrazolo-heterocycle Synthesis Enabled By Self-correcting Amide and Ester Acylation"

Data Description for Isoselenourea-Catalyzed Enantioselective Pyrazolo-heterocycle Synthesis Enabled By Self-correcting Amide and Ester Acylation
By: Martha I. Prindl, Matthew T. Westwood, Alister S. Goodfellow, Aidan P. McKay, David B. Cordes, Michael Bühl* and Andrew D. Smith*

The High Performance Liquid Chromatography (HPLC) data have been acquired using either a Shimadzu HPLC consisting of a DGU-20A5 degassing unit, LC-20AT liquid chromatography pump, SIL-20AHT autosampler, CMB-20A communications bus module, SPD-M20A diode array detector and a CTO-20A column oven; or a Shimadzu HPLC consisting of a DGU-20A5R degassing unit, LC-20AD liquid chromatography pump, SIL-20AHT autosampler, SPD-20A UV/Vis detector and a CTO-20A column oven. Separation was achieved using DAICEL CHIRALPAK AD H, AS-H, IA, IB, IC, ID and CHIRALCEL OD-H and OJ-H columns using the method stated. The raw data files are in .lcd format; the proprietary software which would allow for visualisation of the data and their analysis is Lab Solutions (LabSolutions CS : SHIMADZU (Shimadzu Corporation)). The processed data are in .pdf format, and can be opened using any pdf viewing application, including but not limited to Adobe Acrobat Reader (link) and Google Chrome.
The Infrared Radiation (IR) data were acquired using a Shimadzu IRAffinity-1 Fourier transform IR spectrophotometer fitted with a Specac Quest ATR accessory (diamond puck). The raw data files are in .smf format; the proprietary software which would allow for visualisation of the data and their analysis is IRSolution (IRsolution Optional software : Shimadzu (United Kingdom)). The processed data are in .pdf format, and can be opened using any pdf viewing application, including but not limited to Adobe Acrobat Reader (link) and Google Chrome.
High resolution mass spectrometry (HRMS) data were acquired by either electrospray ionisation (ESI), or electron impact (EI). The data are in .pdf format, and can be opened using any pdf viewing application, or are in .docx format, and can be opened using any word processor (Notepad, Word etc.).
Nuclear Magnetic Resonance (NMR) spectra were acquired on either a Bruker Avance II 400 (1H 400 MHz; 13C{1H} 101 MHz, 11B{1H} 128 MHz, 19F{1H} 376 MHz) or a Bruker Avance II 500 (1H 500 MHz; 13C{1H} 126 MHz, 19F{1H} 471 MHz) spectrometer. The raw data files are in .zip format (containing a number of .fid, .txt, .info, .par, .output and .temp files), and can be opened using any proprietary NMR processing software, including but not limited to NMRium (NMRium - Visualize, analyze and process NMR spectra online), Mestrelab MNOVA (Mnova Software Suite - Mestrelab) and Bruker Topspin (TopSpin | NMR Data Analysis | Bruker). The processed data files are are in .mova format, and can be opened using the following proprietary software (Mestrelab MNOVA (Mnova Software Suite - Mestrelab), Bruker Topspin (TopSpin | NMR Data Analysis | Bruker)).
X-ray diffraction data were collected using a Rigaku FR-X Ultrahigh Brilliance Microfocus RA generator/confocal optics with XtaLAB P200 diffractometer [Mo Kα radiation (λ = 0.71073 Å)], or using a Rigaku MM-007HF High Brilliance RA generator/confocal optics with either XtaLAB P200 or P100 diffractometers [Cu Kα radiation (λ = 1.54187 Å)]. Data for all compounds analysed were collected using either CrystalClear (using ω steps and accumulating area detector images spanning at least a hemisphere of reciprocal space) or CrysAlisPro (PX018 - CrysAlisᴾʳᵒ: an all-in-one software package for single crystal X-ray diffraction) (using a calculated strategy) and processed (including correction for Lorentz, polarization and absorption) using CrysAlisPro. Structures were solved by dual-space methods (SHELXT { SHELX downloads}) and refined by full-matrix least-squares against F2 (SHELXL-2019/3). Non-hydrogen atoms were refined anisotropically, and hydrogen atoms were refined using a riding model. All calculations were performed using the Olex2 (Olex2 | OlexSys) interface. Selected crystallographic data are presented both within the manuscript and in the ESI. Crystallographic data has been deposited with the Cambridge Crystallographic Data Centre under deposition numbers 2410530 – 2410532. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.
The computational data files are in a tar. gz. or a txt. format. A linux operating system is used to access the tar. gz. file. To extract the data, type the following into the Linux system:
gunzip pubAndy-Martha-CompData.tar.gz
tar-xvf pubAndy-Martha-CompData. Tar
This will extract the data as outlined below.
- top_face 3 conformers for each diastereomer
- back_face 3 conformers for each diastereomer
for the lowest top_face and back_face approach
- TS1 Michael addition TS
- TS2 lactonisation TS
- TS3 catalyst turnover TS
- tet tetrahedral intermediate
- tet_pt proton transfer
- lact lactone bound to catalyst
- catAc-carbox encounter complex with carboxylate
- catAc acylated catalyst
- catAc-nuc encounter complex with nucleophile
- prod_1-2 1,2-addition product
- 1-2_bound 1,2-addition tetrahedral intermediate
- TS_add_1-2 1,2-addition TS
- TS_turnover_1-2 1,2-addition turnover TS