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Reinvestigation of a robotically revealed reaction

The Original Article was published on 18 July 2018

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Fig. 1: One of four new reactions reported by Cronin et al.1, and a structural revision of the isolated product.

Data availability

Raw NMR data files for compounds 2a and 2b have been deposited with figshare (https://doi.org/10.6084/m9.figshare.7639703.v1).

References

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Author information

Affiliations

Authors

Contributions

J.K.S. analysed the original spectral data and suggested the structure 2 instead of 1, then carried out all experimental work and constructed the Supplementary Information. J.E.W. did the calculations and prepared the manuscript with advice from J.K.S.

Corresponding author

Correspondence to Jeremy E. Wulff.

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Competing interests

The authors declare no competing interests.

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Extended data figures and tables

Extended Data Fig. 1 Minimum energy diastereomer of compound 1, two diastereomers of an alternative product, and comparison with a known vinyl acetate.

Compound numbering is indicated in red. Chemical shift values (in p.p.m.) are shown in blue.

Extended Data Fig. 2

Proposed mechanism leading to the observed product 2.

Extended Data Fig. 3

Isolation of vinyl esters 2a and 2b, and further evidence for their assignment from hydrolysis.

Extended Data Table 1 Comparison of spectral assignments to calculated 13C NMR shifts for 1aa

Supplementary information

Supplementary Information

This file contains Supplementary Text and Data, Supplementary Figures 1-41 and Supplementary Tables 1-3.

Reporting Summary

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Sader, J.K., Wulff, J.E. Reinvestigation of a robotically revealed reaction. Nature 570, E54–E59 (2019). https://doi.org/10.1038/s41586-019-1176-5

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